Sims 2 dating a vampire
If the sim has the „beg for job“ perk, you may try to use that first, of course.
Also I locked gameplay mechanics that I typically exploit (dates, fresh fish and coffee), made the unlock requirements things I enjoy (like uni), and avoided gameplay I dislike (owned businesses). I suggest keeping them in the same season instead of tracking weekdays. So you might play one household for two 2 days and another one the full 5 days, but you must stop playing a household for that rotation when it enters the next season.
When all households have reached the next season, give them an appropriate makeover and start the next round.
Move them into an existing household (with mods you may ignore the 8 person limit).
Bringing their starting money isn’t strictly forbidden, but it would make things very easy.