TLDR: Realistic tracks, very hard opponent, your choice of pause mode

Personally, I like manual pause mode. I like being able to set up trains for specific loads and set up warehouses without losing 3 weeks of time while doing it. The margins for getting golden check marks are slim enough without that. You can afford to be a little late on one or two objectives with this setup and still get the required 30 points. (I got all gold check marks.)

Going with normal pause mode will give you more leeway on objective deadlines, but you'll need it because of the time spent setting up trains and warehouses with the clock ticking. If you're feeling confident of hitting your marks on normal pause mode (and I'm guessing you're not, since you are reading this!) you could drop opponent difficulty to Hard. This shouldn't be necessary. We're going to hamstring our opponent right out of the gate. (From my own experience, the change in difficulty will change the ultimate buy-out cost from $2M to $8M. At that point in the game, the extra money shouldn't be a problem.)

TLDR: Choose the Engineer

Cheap locomotives and free repair sheds are easily the best money savers for this scenario. We will need to upgrade businesses, but by the time we get there money won't be such a problem. Remember, money saved in the early game will help your snowball get rolling. (We will be buying at least 16 trains right at the start, which will give us an extra $390k for building.) If that wasn't enough, using the Engineer also makes the tactic of putting down 2 small stations viable. It's cheaper than a medium station, denies your opponent access to your cities, and the extra maintenance sheds cost nothing.

I've seen other guides recommend the Industrialist to save money bidding on factories. There are other, better, ways of doing this. As long as we avoid bidding wars (and we will), any money saved building new factories will quickly be lost on the 50% penalty for other auctions. The potential savings are small, and it won't save us anything in the early game.

The Lady and the Gangster may be tempting for the bonus incomes for freight or passengers, but you pay for this with a loss in the other type. And for the Lady, we don't want to be spending money making sure we have the latest trains for the express bonus.

The General might save you up front on track costs, but a lot of that will get eaten up by extra bridge costs.

The Trickster is the only other possibility because of the savings on auctions... but slow tech advances and the fact that we only save $45k at the start of the game makes this a non-starter for me.

TLDR: Profit, not trains. Staff as you see fit.

Research is not a tremendously large part of this scenario.

The starting locomotive is fine for our needs. No track should have more than a 3% grade (until late game where we need to cross over existing tracks a few times). Eventually you will get the Dragon locomotive... maybe even the American. Upgrading locomotives is cheap since we have chosen the Engineer, but only do this if you feel you have a surplus of cash.

Profits are good. Factory profits should be our first buy. Anything that gives freight profit bonuses, or passenger / mail profit bonuses are good. Don't put effort into getting passenger wait times or extra passengers unless it is on a path for something else we want.

Maintenance is good. Anything to speed up or reduce that is good.

It is easily possible to get to the 10% building cost reduction. It is not likely that we will get tunnel cost reduction (useless), bridge cost reduction, or track cost reduction.

Personnel is not a tremendously large part of the strategy either.

Mediators and inventors are almost always good. (Late game mediators will cost you more than you save. Beware.) I rarely use offensive staff -- I need my money more than I need to hurt my opponent. Others... use your own judgement.

Station staff can be useful. Get them if they come up... except tunnel cost reduction.

Train staff can be useful, too. Get them if it is your play style. (I ignored them. My opponent was Beatrice who loves to poach staff.) If anything, get security guards to bump freight prices... especially if you are playing against the Gangster.

TLDR: Buy the meat factory in Sioux Falls, connect to cattle in the south. Connect to Pierre. Connect Pierre to wheat. Buy trains.

Start the bidding wars!
Right off the bat we want our opponent to waste all their money on useless businesses.

1. Start a bidding war for the Brewery in Cheyenne. Raise twice. We let our opponent win. (Pro Tip: Pause the game at the start. Un-pause when the bid window is up to let the auction proceed. Pause again before closing the window. No time will pass.)

2. Start another bidding war, this time for the Meat Industry in Casper. Raise once. We let our opponent win.

Now our opponent owns 2 businesses with the required inputs nowhere nearby, and they have no money.

3. Bid for the Meat Industry in Sioux Falls. It should only cost $150k and our opponent has no money to counter bid. Done.

Start Building

4. Delete the train station in Sioux Falls [Here-after called SF]. Replace it with 2 small stations. Make sure you will be able to lay tracks out around your new factory.

5. Build a medium station in Omaha, and a small station at Collins Cattle near Wichita. Put down track to connect these so that you can make a Cattle : SF : Omaha route. (The extra track at the Omaha station allows you to double track easily. The route from Cattle to SF will pass through without stopping. Maybe you can use a small station and a bypass track, but the game balked at that for me and trains couldn't find the oh-so-obvious route that was there.) Put your station at Omaha on the south side and run your track diagonally up the slope on the edge of the map toward SF. You should get max 3% grade, and a cost less than $135k for that section. The run to Cattle should be under $100k. (You could use passing sidings* instead of running double track but this is a Main Route for 5 objectives.) Set your signals, add 2 supply towers, add maintenance sheds, then...

6. Queue up 8 trains from Cattle (minimum 8 cars), to SF (priority meat), to Omaha. (I put refrigerator cars on mine for the extra revenue delivering meat to Omaha.)

7. Build a medium station in Pierre and connect to station #2 in SF. Use a single track with ~4 passing sidings. Curve the track north of the cotton farm so that it runs diagonally up the slope. That will reduce embankment costs and should give you a max 2% grade and a cost under $150k. Set signals, add a supply tower and maintenance sheds.

8. Queue up 4 trains, automatic; 2 from each end. You could put refrigerator cars to get extra revenue from the beer we'll be shipping.

9 Put a small station at Rice Manor (wheat farm north of Pierre) and connect it to the second station line in Pierre. Track should be less than $60k. Put in ~3 passing sidings, signals, a supply tower, maintenance shed. Queue 4 trains to run Wheat (minimum 8 cars) to Pierre. This is another food run, so put on the refrigerator cars.

At this point we have used all but $150k (or so) of our starting funds after taking out the 2 bonds that we are allowed, so it's time to let things play out a bit. Un-pause and check that all your queued trains are doing what they should.

At this point we have a set-up that will
a) be getting us a decent profit on a beer / meat line,
b) allow both Pierre and SF to grow to start to get that 400k population goal, and
c) get us the cattle to SF, meat produced, and meat to Omaha** tasks.

* For passing sidings, build ~18 miles of parallel track and put one-way signals at the switches (like in the tutorial / campaign 1). You can also do ~30 miles with a supply tower in the middle so that supplying trains don't sit and block your single track.

** Some meat will get diverted to Pierre. That's OK. Growth in Pierre is more important than meat to Omaha right now. Once we connect up Pierre and Rapid City we can stop this.

TLDR: Add a line from Pierre to Rapid City, and from Rapid City to Reed Fattening. Buy the Meat industry in Rapid City. Stop sending meat from SF to Pierre.

As soon as you can afford it, put down a small station in Pierre and another in Rapid City. Connect using a single line with passing sidings. Put in signals, a supply tower, and maintenance sheds. Queue up 4 trains, same as SF to Pierre. This is our second profitable Beer / Meat line. (Refrigeration cars highly recommended to cover both the meat and beer deliveries.)

At this point, edit the SF / Pierre train routes to ban carrying meat away from SF. We want all this going to Omaha for the objectives. Pierre can get meat from Rapid City.

Buy the Meat Industry in Rapid City before connecting to Reed Fattening. It will get more expensive after that, and we really need to have that meat production! Our opponent should still be recovering from our earlier bidding wars, so shouldn't give us any trouble.

Then connect up to Reed Fattening with 2 more small stations. Use parallel tracks here. This is another critical connection. (For cost savings, you could use passing sidings to start, then come back later to expand the capacity.) Signals, supplies, maintenance... you know the drill. Queue up 6 trains to run 8 cars of cattle to Rapid City.

The meat connection will help us to get the Meat Production task. We'll switch the routing to get it to Omaha later. Right now the meat is needed to get population growth.

NOTE: During this stage, pay close attention to the population in SF. At 40k, an industry slot will open. It will likely get filled with a Sawmill (useless) unless we get there first. Start saving and get your bonds ready to get $400k to drop in a Weaving Factory if you get the chance. This will allow continued growth in SF and Pierre which could be critical. If you manage it, and you REALLY should, connect the Cotton Farm to your line from SF to Pierre and run 2 trains. (Tie it in to your existing infrastructure. No sense spending tons more cash there.)

NOTE 2: At some point, drop a small station at Kelly Ranch. Place it so that it "crosses the T" of your opponent's line. We don't want them to close the loop from Kelly Ranch to North Platte. We will need that ourselves. This block should convince them to expand north-west instead.

NOTE 3: If you see a connection bonus that you can make with cash on hand, do it. Then delete the line and station. You get the cash from the bonus for free.

TLDR: Connect Rapid City to Bismark. Connect Bismark to wheat. Connect North Platte to Pierre. Connect Kelly Ranch to North Platte (warehouse). Make any and all easy connections to population centers.

This is probably the hardest section. All main objectives to 1953 will be ticking off nicely and should finish in half the time required. The Big Drive is on for 400k population and 20 meat production. Our first (and toughest) task is population.

Start with another pair of Beer / Meat connections.

Expand a station in Rapid City and run a line with passing sidings up to a small station in Bismark. Signals, etc. and run 4 trains. Put another small station in Bismark and connect to another small station at Rice Manor. Signals, etc. This is a short run; 3 trains should do it.

Expand a station in Pierre and run a line down to North Platte. Position your station there so that you can run a line toward Omaha later. Bypasses, signals, etc. and 4 trains.

At this point we want to start connecting to any population center we can easily get to. The Beer / Meat lines will be generating a good cash flow, and we can periodically buy out and renew our bonds for a cash infusion. Don't forget to check your infrastructure to make sure goods are flowing. Add some trains to your cattle lines if supplies are running short.

We want to connect to the big population center of Denver, but we'll have to go through Kelly Ranch to get there.

Build a warehouse that connects to North Platte on the south side. Position it so that lines can be run from there to Omaha later. Connect the warehouse to Kelly Ranch. Double track as always on the cattle lines. Set the warehouse to accept cattle. Signals, etc. and run 6 (or so) trains there.

Run a single line from Kelly Ranch to Denver. Just lay a single track to a small station as we don't plan on using this line. Use the same small station to connect to Cheyenne. You may have to cross your opponent's tracks to get there. This is a short run. You can double track it and run 2 trains just to make a bit of profit. If you can, put a second small station in Cheyenne to keep your opponent out. If you end up needing an extra 13k population, you can run a line up to Casper.

Put a small station in Amarillo and run a line with passing sidings up to your warehouse. Set the warehouse to accept meat and run a few trains. Use just enough to get the small meat production rolling. Don't connect to the cattle yet; we want to buy the Meat Industry before we make it more profitable... later. Population first.

Now start running single lines to small stations in nearby population centers. Again, we're not going to use these lines. We just need the check mark... and quickly! Dodge City and Wichita are easy choices as they are near existing lines. Miles City and Billings in the north can connect into the lines near Reed Fattening. They have decent populations of ~18k. Connect anything else that you can until you get the notification that you have 400k population. Then delete all those extra lines.

TLDR: Buy and upgrade meat industries. Start delivering to Omaha.

Use the extra cash from selling off the lines to Dodge City / Wichita / Casper / Miles City / Billings to buy the Meat Industry in Amarillo, and connect up to the last Cattle Farm. Upgrade the passing sidings on the Amarillo / Warehouse line to a full double track. Run more trains.

Now we change focus to meat production and delivery. We're on the final stretch! If you made it this far with all gold check marks, you are in good shape. Just a few more hurdles.

At some point you will need to buy out a cattle ranch. Make sure you do this early enough that you don't need to upgrade it to get the production target in time. (Before the middle of 1852 or as soon after that as you can manage.) They will all likely be level 2 or 3 by now. Pick the cheapest one. It will likely cost you $700k to $800k. Your opponent is unlikely to be able to afford to challenge you.

We want to buy an additional Meat Industry to make sure we can meet the production quota. We already have SF, Rapid City, and Amarillo. We can buy the one in North Platte -- we are already supplying it.

In order to produce more meat, we need to start clearing our inventory to make some space. Fortunately, dumping it in Omaha is a task we need to do!

Start by putting another warehouse down near North Platte (on the north side, not connected). Expand the small station and connect to the warehouse. Set the warehouse to accept meat and start moving the stockpile. Run enough trains to get a constant flow; set all to minimum 8 cars.

Expand a station in Rapid City, and connect to the same warehouse. Run more trains. Edit the routes going out of Rapid City to ban meat going to other places. (You can leave 1 train on each line allowed to run meat to keep the Beer / Meat profitable.)

Use the massive cash flow you have to expand your Meat Industries. This is where the Engineer's flaw will show. Your snowball should be strong enough to cover this. Upgrade the industries you own to level 2. Make sure that your cattle lines can keep up. Add trains as needed.

When your warehouses start filling up, create warehouses connected to Omaha -- one north, one south. Expand your warehouses near North Platte and connect the added platforms to the Omaha warehouses. Set the new warehouses to accept meat. Run trains as needed to keep the warehouses near North Platte empty.

Keep doing this until you hit the magic target. Upgrade Meat Industries to level 3 if you have to.

If you have been following along, you should have plenty of time left for this expanded production to deliver the required 1000 meat to Omaha. If not, expand more. You can buy the Meat Factory in Denver if you have to. You or your opponent can deliver the cattle.

TLDR: Deliver the meat. Buy your opponent.

By now the production of meat is at a point that it is only a matter of time before all the meat objectives are checked. All that remains is buying out your opponent. Cash should be rolling in from the Meat / Beer pairs, the factory profits, and the meat deliveries.

As money permits, start buying shares of your opponent. Cash and renew bonds. Buy more shares.

From then on it is just a matter of waiting out the clock. You can use spare cash to upgrade any weak points in your lines. Convert passing sidings to double track... upgrade cattle / meat shipping and processing... add extra trains where needed.

The last task I had to do was 1000 meat delivered. That was accomplished 3 months ahead of schedule for the final gold check mark. Final score: 32.