"Fairy Race"----sorry didn't understand that. Were you MC & 1st slave both fairies?
"Sell everything you have"---BEEN THERE< DONE THAT FAR TOO MUCH! [& wind up broke!] Should be noted as said elsewhere, good weapons/armor/tools cost $$$, so selling too much can really make you take a big hit.
BAD LUCK w the quests is part of what this post is about. [Assume even w 5 charm, you can't get enough Quest points by D28 (once in rare while I get lucky, ESP if give myself *HELP*)] As you say, Quests for items you can't get (or can't get enough of) "DUNGEON CLEAR" Quests (often *IMPOSSIBLE* 1st 14 days! Bandits aren't too bad---but how about "UNDEAD MONSTER HUNT?
Many, *MANY* of the quests need to be re-balanced, *OR*, simply not allowed 1st 21 days.
Your "3 debts" I assume you mean D28???
Actually, $$$ PRICE (1 WT I've seen posted a lot says cost doesn't matter & that's complete BS!) cheap as possible *PLUS* Hi PHYSICS (growth is nice, but not Req;) I'd MUCH rather have GR 1 PH 5, than GR 5, PH 1 !!! [not that newest version changes some tasks to Wits that were prev Physics]
You didn't mention Upgrades much----I've found it *VERY* difficult to do Quests *PLUS* resources/$$ [GREEDY BANK!] w only 5 workers, so Rooms upgrades are a must. (done some where avoid some quests, LESS Upgrades/people, but otherwise----10 [?] rooms is a min?
Never tried fairy, sounds interesting. (usually get "Scholar" 4 their heal) EITHER WAY, WEAPONS/STAFFs cost $$$ that I rarely have avail. (unless cheat ;-)
I tend to go with hi dam chars ----everybody "heals" even while working----so as long you have enough hp to fight & not die & still go back to work...
2nd run is where you were "fairly blessed early quests",so " it was overall significantly easier." LOL EXACTLY MY POINT! [I think many of the quests should be re-balanced, OR not allowed 1st 14 days.
FYI fishing is usually much better profit than hooker (you didn't mention version----*MANY* new restrictions in newesst version, including no fishing (I hear fishing a lot) @ start. ) It's very similar to your idea: *** Make $$$ *** OR*** do Quests (but not BOTH!)