It's my first try for a guide and it's even not in my first language, so please forgive me for certain mistakes and spelling errors (don't stop correcting me).
I will try my best for this and accept gladly help.

Finished Chapter 2. Next: Tower of Self-Improvement

Most of them grant you a skill and when you collect enough BP, it becomes permament.
The skills with stat boost (atk, def, ...) raise the stat about 10% inclusive equipment.
Fitness Reader (HP) and Dictionary Reader (MP) grant a flat and a percentual boost (I realised that my characters getting different amounts for these stats but double base stat didn't mean double extra points).
However, books like "Do It Youself" and "Diet" seems to have a influence on resistance against certain status effects. How can't I say now. Either lowering the chance for getting the effect or get ridding it off faster are my guesses. I will update this definitly when I get more info about this.

In the north of societyville you can find a guy who combines items.

coffee grounds + hot water = coffee (150MP recover ooB, sells for 250$ each)
lettuce + bread = 5x sandwich (500HP recover in battle, sells for 10$ each)
frame + wheels + chain = bike
wood + tool = 5x hobby coins (you can make them to money somewhere)

Coffee grounds and hot water getting dropped at the two lowest level areas in the game, so you can get them really early, but they don't drop often, so it can take a while until you have enough of them.
Lettuce and bread are buyable in the same town for 10$ each per unit, so you can make profit by selling the sandwhiches.

Here are the characters listened who join your party. "ooB" means out of Battle. I try to keep this list at story.

Bob/MC

recuit:
from beginn (level 1)

traits
- slightly above average stats
- learns skills in every category
- position in battle: depends on equipment




Randall

recruit:
first room mate (level 2)

traits
- begins with low equipment (no community, no book)
- owns fedora (higher chance for getting attacked)
- high HP, low SPD, very low MP, need less exp for lvlup
- learns skills in support, personal, human (single target)
- position in battle: meat shield/tank, last hitter




Gina

recruit:
first possibility in Port Nostalgia (level 4)

traits
- owns cooking stuff (stronger item effects)
- high SDF, low HP
- learns skills in support, personal, work
- position in battle: support




Alayna

recruit:
Tower of Self-Improvement, Floor of Arts entrance (level 6)

traits
- owns Idealism (regeneration)
- high MP, very low HP
- learns expensive skills in support, personal
- position in battle: glass cannon




Cecelia

recruit:
Societyville, library, after taking her quest (level 7)

traits
- average stats, high SAT
- learns expensive skills in support, personal, human (group attacks)
- position in battle: nuker




Lisa

recruit:
Relationship forest, shrine of marriage, after helping her (level 6)

traits
- high SAT and AGI, low HP
- learns skills in support, mind, human
- position in battle: mostly healer




Caleb

recruit:
Relationship forest, shrine of marriage, after helping her (level 6)

traits
- decent HP and LUK, high MP and AGI, low ATK and SAT
- learns skills in support, personal, human
- position in battle: first aid after battle until better goal, then basher

I won't list everything what you can find because I assume you would follow those tips:
- you explore automaticly each map you come and talk to everyone and open chests
- Save often. Because of the part nonlinearity in the game, you should use multiple savings.

The first parts are pretty much linear, so i fell in some kind of railroading to get everything and everyone.
After a certain stage, I state only map infos and noteable things.

I would mention everything that is not noteable at first sight, if it not slipped on me.

We begin in the location "castle of sanity". SW you find a chest with Ring of Sanity. S is the entrance to the south of the continent, but you can't go there now. SO you find on the table a Fitness book, your advisor and a soldier who allows you to send troops/money to reduce your enemy army/cred dept. O you find stairs to a room with infos about the game mechanics. NO is your bed. When you go sleep, game time procceeds one month. N is the entrance to the north of the continent. NW is the Altar of Finances with stairs (locked now) to rooms with expensive monsters.

Your advisor says you need a room mate and a promotion for managing this month. We go N trough the entrance.

The north of the continent

notable encounters:
- single monster "unpaid bill" (transforms after his first turn into "late bill", a much stronger monster)
- monster group with 7 members (for this group you should have at least 3 group members)

drops:
- coffee grounds

W relationship forest
NW shrine of patience
N dungeon of work
O port nostalgia
S castle of sanity

We go to the relationship forest at first, open the chest, talk with the girl, go S and talk with Randall and follow his advice. Be warned, at this point the monsters here are a little bit too strong.

relationship forest

notable encounters:
- 2 monster groups with 5 members

drops:
- hot water

NW to Sociityville, tower of self-improvment, bank/mine
SO Singleness Glam (late game zone)
O shrine of room mates, shrine of marriage
NO back

Now we go the dungeon of work. Bob should have level 2 for the skill paperwork (helps against the monsters in the next fighting area). Go N to the dungeon of promotion. Save before you enter.

dungeon of promotion, first promotion

notable encounters:
- trap monster on one chest
- single monster "boss" (run!)

Open all chests. You get a few heal items, a new goal and a new community. Fight the area boss.

Area boss (New Obligations)
- count as personal enemy, causes unmotivatet (blind)

A few rounds with hitting and it is beaten. You are out of the dungeon now. Go to castle of sanity and sleep. A scene occurs.

After the lost fight you're now in the 3rd month. We talk with our advisor and go to Port Nostalgia. We give Jar 20$ for a coffee two times. Then we talk to Gina and invite her in the group. Now to Mom'n'Pop Embassey. On the table lies a Diet book. We're going through the relationship forest. On the way we pick up a red flower so we can go through the relationship barrier and uncoil the rope.

We make a stop in Societyville to buy a first-timer coffee (50$, we get Coffee Shop Friends), talk to Emily, buy some Lettuce and Bread, make Sandwiches and coffee, sell some of them, repeat it a few times to get money, go into the library, buy free books, go into the book shop, use part of our newly earned money for books we didn't get in library, leave the town and go SO to the tower of Self-Improvement, Floor of the Arts to get our next member, Alayna. We leave immedatly the tower and go back to Societyville for another member after we ensured that all our current party members are at level 5.

We going in the library, talking with Cecelia about what's upstairs. We can go up the ladders now, where Cecelia already waiting for us. We must take her in the active team, so i put Gina on the spare bench. Her skill Support works good from there.

library, upstairs

noteables:
- the enemies causing lazyness (silence) that not get cured automaticly at the end of the battle.

Area boss (Anti-Intellectualism)
- can attack the entire group causing lazyness (silence) and unmotivated (blind)

After we beat the area boss in the 3rd round, we take the last lying book and jump through the hole. By walking a little bit we get rid the lazyness status. Next we walk through the relationship forest. Before we reach the exit, Randall notices something on the shrines.

It's Lisa, who tries to fix the shrine of marriage but being stopped by a White Knight. After we decided to help her, she wanders in our party and Alayna goes on the bench.

The next soon-to-be member is Caleb in Port Nostalgia but at first we must fight against Friend's Depression.

Friend's Depression
- personal enemy
- causes depression (poison) on entire group

Alayna's skill makes this fight easy and Lisa's Clarity cures us after the battle.

In this chapter we are going to solve the Tower of Self-Improvement (as far as we can in this state) and getting the second last member, Frank.

But before that, we need refreshing our group (Until now, I didn't use any items for healing my party, in the tower I will use coffee). There are a few options for this:
1. go sleep and let time go further (before you sleep reduce second loan at least under 2000$)
2. use the sandwich trick and get enough for a full meal in the restaurant in Societyville (500$)
3. grind coffee grounds and hot water for coffee (the areas are now much under your level and with the virture Idealism you can heal the active members so you don't need MP; you can use this to learn book skills, too)