As someone who plays management games mediocrely,
skill issue. Really, even if you get shafted hard in wk 1 with quests it's not very hard to clamber out; just sign with fighters or mage guild, go adventuring, grove and goblin caves are easy ways to get tons of exp and decent gold [sell loot], use gold early to buy armor and just run around.
If you can't get 500 pts after paying 4k, you're too slow and not spending enough exp on upping charm factor for mc; if you trihard, you should reliably get 500 pts at on or around the 4k payment