There were some things I wanted to check out, so I'm gonna do a playthrough and talk about what I'm doing. Maybe someone will find it helpful. It's my second playthrough so I often try to avoid progressing time, just for fun. Anywhere I use sandwhiches feel free to use healing spells, and rest whenever you want. There's no downside to resting, and in fact there are some parts of the game you can't get to without doing so.

edit: I abandoned this project, but still follow the thread offering helpful advice. I don't think the playthrough is ever going to get done though.

Month 1:
Went to the relationship forest and got Randal to join the party
Went to work for the first promotion dungeon. In the dungeon I just attacked stuff. Try not to dally too long and run out of MP.
Boss! New Obligations
Party: Bob/Randal level 2/3
just attack, and if someone gets below 300 have them heal themselves
Go back to castle sanity, talk to the guy in the blue hat, and sleep

Month 2:
go lose to the debt commanders. They seem weaker than their late-game version, it might be possible to beat them, but it would probably be 10+ hours grinding mobs in the plains of Sanity.

Month 3:
Time to collect allies!
go to port nostalgia, and ask Gina to join me
Tower of Self improvement get Alayna to join me by entering the floor of arts, but since the floor will mess me up I leave immediately

I go into societyville. At the farmers market I buy bread for $10 and lettuce for $10. I go to Jacob's house and craft those into 5 sandwiches. I go to the restaurant and sell 5 sandwiches for $50. I do this for a while until I get bored. While this loop costs Bob 0 months, it uses too much of my time, and is terribly boring. A stack of sandwiches has $600 profit, and takes a minute or two, so getting Bob out of debt just by crafting sandwiches would probably be the two boringest hours of your life. feel free to do so if you want.

I go to the library, and get 11 copies of each book, since they're free. I equip everyone with history books to boost xp growth, then talk to Cecilia about what's upstairs. Go up there and she joins the party. I replace Gina and we go through the dungeon. It's very easy, including the boss
Boss! Anti-intellectualism
Party: Bob/Randal/Cecilia/Alayna levels: 4/5/7/6
I just attack for a few turns and he dies

I go back to the relationship forest and talk to Lisa
Boss! White Knight
Party: Bob/Randal/Cecilia/Lisa Levels 5/6/7/6
I think his "concern trolling" attack does a percentage of current health, and can't actually kill you. Either way he goes down easy to normal attacks.

I go to Port nostalgia to help Caleb out with his depression.
Boss! A Friend's Depression
Party: Bob/Randal/Cecilia/Lisa Levels 6/6/8/6
I heal anyone who goes below half HP, being depressed stinks, but there's not a lot to do about it at this stage of the game. he eventually falls to normal attacks

I go to the basement below the shrine of income (let's call it the dungeon of expenses) The monsters here inhibit your income, are fairly easy, and give great xp
The food bill 1 monster is trivial
The Car expenses 1 monster is very easy
The Utilities monster is easily defeated
The phone monster is a little harder, but is quickly pacified

Boss! Rent Monster
Party: Bob/Randal/Cecilia/Lisa Levels 8/9/10/8
At this level Lisa can't really survive this fight so she ends up on the floor. I put top priority on healing anyone below 700hp, which means if the boss uses "stubborn landlord" the whole team spends their turn healing. I eventually grind him down, but about 50 sandwiches are consumed in the effort. (I could use healing spells, but I'm trying to avoid sleeping for fun)

Since I'm running low on sandwiches I go back to societyville. I buy some "rethink life"s, and run back and forth selling sandwiches to build up some cash. I also go to the book store and buy the books not available at the library. Then I head for the tower of Self-Improvement

If you haven't done so yet, check into the second promotion dungeon. In my first save I was able to do it with an average party level of 8. the guys walking around are pretty tough though, so maybe waiting until getting a few more levels wouldn't hurt

First I head to the tower of mind. The entry boss is stupidly easy, and I explore the floor
Frank joins the party
Boss! Stupidity
Party: Bob/Randal/Cecilia/Lisa Levels 10/10/11/10
Randal is on sandwich duty, since he's otherwise useless. If the boss uses "stupid pattern" at this level it always kills the target, so I use a few "rethink life"s to get through the fight.

Next I head to the floor of Body. I go down all the other wings and gather some nice gear (and some levels) before heading south to the boss.
Boss! Preventable Death
Party: Bob/Randal/Cecilia/Frank Levels 12/13/13/10
If he uses cloud of laziness too many times the fight becomes very hard. Any equipment that protects from laziness helps, but he goes down pretty fast

I run to town and refill my sandwiches.

Floor of Society is next on my list, and it starts with a boss, a boss who uses misguided cloud, which is *bad*, so I go to town and buy two guidance charms. then equip my party so all 4 are immune to the misguided status
Boss! Social Isolation
Party: Bob/Randal/Cecilia/Frank Levels 12/13/13/11
as mentioned, I made my party immune to misguided, which made the fight a lot easier. Misguided cloud still does a lot of damage. you may have to try a few times until she uses some normal attacks instead.

The rest of the floor is just walking back and forth. some old lady tells me there's a secret here, but I have yet to find it...


my insatiable minions are once again low on sandwiches, so I go make more, and sell a few batches. At this point I have the money required to pay off the first credit card legion, and it seems like a pretty good time to do so.

edit: I abandoned this project, but still follow the thread offering helpful advice. I don't think the playthrough is ever going to get done though.