This game looks quite hard to get into...is there any guide on how to get your bearings?
My suggestions: Start with Large Physique and Physically fit/Good at Sports. Punch your way to and from School, while you find an easy part time job, like Dock Working or becoming a waiter/ess. First day, go to the temple and ask for a chastity belt and join the temple. If you maintain your V card for a month you get a few thousand dollars when they check (every month). If you win the school events, you also get quite some money.
Other than that, depends what you are into. The game is very sandboxy after figuring out the main love interests and times things happen, you are quite free to choose a direction and explore.
A few to keep in mind: If you are in Robin's Room from 7-8, you can go to school with Robin, automatically evading any hostile events on the way. Same in front of the School from 15-16, you can go Home with Robin. Or you can go deep into the forest safely and swim/explore the Lake and area... the kids return between 20-21, so make sure to not stay alone in the forest.
If you are into Bestiality and Tending, the Forest, Moor or Farms are the best options. If you like dancing, some lessons and then the Strip Club are safe ways... If you use your hands a lot, the Spa is a good place and you can also steal things and break into houses... doing everything is a bit difficult, as is staying on the Robin route, due to the amount of money you need to pay every week.
Once you've played a couple of times, maybe even with cheats, you'll get a hand of the basics and be comfortable in trying or discovering things out.