Get caught earning while claiming Job Seeker's Allowance and Invalidity Benefits

To get this one, first you need to get on Incapacity Benefit. You need to run out of energy and pass out. If you have already done this and have the get well soon card, you can skip this step. You can easily waste energy with the hand mixer, just mix nothing over and over till you pass out. Then you wake up in your caravan, with a get well card from Kashmirian, the job centre lady who found you passed out in the street.
Go to the job centre and talk to her, and use the dialogue line about having hurt your back. This will get you on Incapacity Benefit. Make sure you are signed on for Job Seeker's Allowance too. Then go work a few shifts washing pint pots in the pub, and it won't be long before somebody dobs you in and you get the achievement. It is best not to save after this, or if this is your first offence, go down to the police station and ask them to let you off with a caution.

Become permanently afflicted from smoking

Check your stats in the notebook. Your lung capacity will be listed at 5000 litres. For every cig you smoke, you loose 100 litres of capacity. Getting your lung capacity down under 1000 will give you black lung, and your lungs will be permanently damaged. You can buy cigs from the machine in the corner of the pub. Press a button, and crouch down to pick up your pack from where they come out at the bottom. Don't bother buying more than one pack at a time, you can only hold one. To spark up, click on your notebook, and select the cigs from your toolbelt. Smoking is a very quick flick and puff, so you can burn through them fast. It looks like there are 10 cigs in there, but you seem to use them up 2 at a time. (another bug?) It will take about 10 packs in a row to get the achievement. Chain smoking can use up your energy, so stop for a pint now and then if you run low. You can get the achievement in one day in the pub with no problem. Since the effect is permanent, it is best to get it done in one day, and quit without saving your game by sleeping.

Become obese

To get this one, you need to put on weight. This is as easy as going to bed with a full belly every night for a week or two. As the name of the achievement hints, this is as simple as eating two meals. Your calories max out at 4000, but anything above 2500 should result in a bit of weight gain. Hit 96kg and you should get the achievement. The last few kilos seem to be harder to gain, so you might want to max out your calories to 4000 before bed for a few days in a row for this. To loose the weight again afterwards, simply sleep through a week or two without eating.

Get banned from the pub

This is as easy as tossing around a couple of bottles or glasses. Hold G to throw. This will get you banned for a day. Or take a piss on Tamsin, that will get you banned for two weeks. It is best not to save your game if you get a long ban, because it also bans you from Tamsin's bap van, and you won't be able to eat. You won't actually die of starvation or anything, but you won't be able to sprint anywhere so it is best to not save, or sleep through your ban.

Purchase all items from the tool catalogue

To get this one, you have to buy everything including all the colours of paint and all the storage buckets.

Go to jail

The quickest and easiest way to do this is walk into the police station, and piss on the copper. That will get you a night in the cells, and the achievement.

Rent out a property with 3 floors

Exactly as it says. Make sure your third floor has a staircase and a full external wall, so it generates a ceiling. You can even make it look like a dormer window if you want to make it look pretty or convert an existing 2 story house with minimum fuss. Just surround it with roof frames to get the look.

Accumulate £100 from benefits

Go to the job centre and sign on. You will get £3.57 a day, so it will take about a month to get this achievement. If you get on incapacity benefit too it will go faster. The rate of benefits goes up slightly with inflation as the years roll by, so if you are in the end game it might take even less time. Just be aware that you can't sleep multiple days in a row and still get paid! you have to wake up every day and collect your money. Check your notebook to see how much you have already claimed, you might be closer than you think already.

Skip the tutorial

When you confront Jimmy as he is breaking into your site, tell him you don't need any help. If you don't already have this one, back up your save, start a new game, and tell him where to shove it. You can back up your save by clicking save data in the main menu, then copy the whole "landlords super" folder to anywhere convenient.

Retire in a house worth at least 40k

The key to getting a very high house value is sheer size. If you lay as many foundations as you can fit on the site, and add some no fines walls and enough to satisfy the minimum build requirements, this already gets you pretty close. Take it up to 2 or 3 floors to make it even bigger, and it will be worth silly money. If you already have a nice house that isn't worth enough, try building an extension. If your house value is very close, add more furniture and fittings. Once your house value is high enough go see Mitchell. Make sure your loan is paid off, and hit the retire button.

Perfectly satisfy a Yuppie tenant

First you need to satisfy the build requirements for renting to a yuppie. At least 2 floors, at least 300 sqm, at least 30k house value. Yuppies like furniture out of the Harolds catalogue, but it isn't strictly necessary. The condition of the house is more important. With your freshly built house in perfect condition, it should only take one tenant to get the achievement. Pick a tenant with a high satisfaction rating and a short tenancy. When they leave, you should get it.

Roll a jackpot

To get this, you need to get the jackpot out of the fruit machine in the pub. The best way is to follow this handy guide. The only useful advice I can offer here is to make sure you have a good frame rate, this makes the quicktime events much easier. If your frame rate is low, try lowering the graphics settings, and waiting for a day with clear weather since rain typically reduces your framerate a lot. To get the jackpot, don't cash out your winnings, just keep playing until you get it. You will need about £20 to feed the machine before you get it.

Complete 3 jobs around town

You need to do Tamsin's pub wall job, Kashmirian's patio foundation job, and Totter's church roof job at least once each. Check the boards in the job centre for the jobs.

Sample all alcoholic products, including bottles, shots, glasses and pint variations.

Simply do as it says. Do note that it says "sample", you don't have to finish the whole drink which makes things a little easier. None the less, you will have to spread this bender out over several days. Totter at the scrapyard will buy your half full bottles, so you can get back some of the money you spend. Try to work through them systematically so you don't forget what you have already drunk. If you get a hangover, the best option is just sleep it off.

Perfectly satisfy a Grafter tenant

First you need to satisfy the build requirements for renting to a Grafter. At least 2 floors, at least 200 sqm, at least 20k house value. Grafters like furniture out of the Agoost catalogue, but it isn't strictly necessary. The condition of the house is more important. With your freshly built house in perfect condition, it should only take one tenant to get the achievement. Pick a tenant with a high satisfaction rating and a short tenancy. When they leave, you should get it.

Read 20 newspaper articles

You will read the paper every time you sit on the toilet, and there is a new paper every day, so this one is as simple as going to the bog 20 times on different days. You can skip time on the toilet, and also get some useful gameplay tips from the papers. Check under "Stats" in your notebook to see your progress towards this one.

Climb ladders for 306 steps

As it says. You should get this one eventually through gameplay. Check under "Stats" in your notebook to see your progress towards this one.

Rent out a property that is 25 metres squared or smaller

Check the last page of your notebook to see the size of your house. For reference, a full sized foundation frame at 250l is 9.5 sqm, so 25 sqm is about 2.6 foundation frames. Experiment with the wall layout and keep checking your notebook. Buy the smallest furniture options you can. The wall mounted oven is a good idea, and you only need a kitchen sink or a bathroom sink, not both. Some furniture items will stack, you can put the TV on top of the table for example. Don't worry about minor details like having enough space to move around in there, anything will do if you can cram in enough stuff to meet the minimum build requirement. Once you have done this, rent it out to some lout and get your achievement. Just so you are aware, it IS possible to make a liveable space within those size constraints, but that takes much more effort than just getting the achievement.

Perfectly satisfy a lout tenant

This one is easy, as long as the house isn't unlivable, you will get this one. Pick a tenant with a high satisfaction rating and a short tenancy. When they leave, you should get it.

Retire before 1984

To do this, you need to pay off your loan and have a liveable house within 30 days. The only way to do this is to sell your house as quickly as possible and build a new one to retire in. See my speedrun guide for how to do this in as little as 4 days.

The short version? Consult the map to find all the abandoned furniture items to save yourself some money. Remove all the interior wall frames from the house and sell them to raise some more cash. Get the house to the minimum build standard and sell it. Then build a quick and crappy house to retire in.

Mix perfect concrete, mortar and no-fines

Check the building manual section of your notebook. If you have already made a perfect mix of something, there will be a "prime" recipe there. See which ones you are missing, then mix up a minimum size batch as follows:

Concrete: water 2l, cement 3l, sand 5l, aggregate 10l
Mortar: water 2l, cement 3l, sand 15l.
No-fines: Water 3l, cement 1l, aggregate 6l.

Make £100 selling scrap

Check the first page of your notebook and you will see your earnings from selling scrap. Anything you take to Totters yard or dump in your skip will count towards this. Clean up your building site by chucking everything you don't need into the skip. Run around the map looking for broken TVs and filing cabinets, these are the most profitable scrap. If you have bought some furniture or fixings in error, the only thing you can do with them now is chuck them in the skip. It should be easy to get this achievement through normal gameplay.

Lay a brick

Make some mortar in a cement mixer from sand, cement and water. Buy or steal some bricks, buy a trowel and lay a brick. Fill your trowel by left clicking on the mixer, Left click to place a blob of mortar, right click to smooth it down, then pick up a brick and place it. You should have got this one in the normal course of fixing up the house.

Union's not going to like this
Place a roof tile in the rain

Get up on the roof in the rain and place a tile. The starter house is low roofed enough that falling off won't hurt you. Much.

If I told you to jump off a cliff, would you?
Pee on the bus stop

See the graffiti on the bus stop that says "piss here"? Do as it says.