So this might qualify as cheating, but. If the first set of quests looks bad, I just start over. They need to be pretty bad for me to give up though. Next, you can go all min/max on MC and first slave.
My favorite is a Seraph fighter MC (female or futa for Valkrie) with a Dark Elf scholar for first slave.
To make quest more rewarding set the MC's social factor as high as possible, remembering that Fighter class requires 2+ Physics factor. A high Social factor for your MC boost the Guild quest rewards.
Set the first slave's Magic, Growth, and Tame factors high. I side with the Mages. This gives a boost to their rep points and gives the mage a decent staff. I set their starting sex traits to Life Power (healing from sex) as this permits doing more dungeons.
Get 1st slave's loyalty up quickly ( if you want to use submission, set Timid factor high instead of Tame).
Get Druid as 1st slave's 2nd class. Pick MC's classes to increase HP and Physics.
Get Daisy as soon as you can.
Set her and the 1st slave to fishing (more money per day than whoring at this point).
Now hit dungeons as much as possible.
If you can, make the first Tailor or Forge upgrade. This usually takes a while unless you stumble upon a forge hammer.
You have 14 days to make 1000, so 72 profit per day. Now, you will need to buy weapons, but often you get a decent one for the first fighter quest.
The Servant quest often depend on luck at first, so don't worry about them unless they are easy. The Servants will always support you for Mayor, no matter your rep points with them.
Put off starting the civil arc until at least day 27. Some of the combat is difficult and you need equipment and classes to survive. Also by this point you should have a decent amount of coin.
Don't increase the number of slaves too quickly. You'll need to build them rooms and keep them Loyal(or Submissive).
This is one way to survive, but people have followed other strategies with good success.