I did another run from scratch, the saves are included : https://drive.google.com/drive/folders/1xyqkgYZxHZSQpY8wVlsIjvLYuLgXTv0n?usp=sha...
It is not a day by day save though.
I did encounter some bandits with the nimble and precision trait early on D3 or D4, my squad miss a few hits but I was able to kill them, not an impossible foe to kill imho. I must say when I play normally I steam rolled them. Later (around D15?) I even encountered someone with 90 EVA, 3 mages attacking him and he met his end.
Finished the Loan Quest on D23 and had already 3.3K in gold + materials from dungeons.
Regarding incomes my best hooker was earning 204 gold/day and she could be trained to earn way more ( the cap is 210 in CHA and she is at 134). The 2nd gave 174 gold/day. For the most part I had only 2 hookers. The last 2 slaves were bought specifically for assignment quests.
Concerning dungeons, by the beginning of the 2nd week I can steamroll all the easy ones and potentially do at least 2 per day (if I don't loot but I do loot the area). For 100 gold they are worth it, I obtained great loot in there (staves, armor some made from adamantine and obsidian too, raw materials) By looting the dungeons I could if I wanted build some mansion upgrades without having to buy them in the shop.
I did all the easy quests on the notice board, no MED quests so yeah quite accessible.
I'm repeating myself here but I don't see what prevent you from having successful runs. It's all about time/resource management.