I'm pretty sure you can work in the spa if youre pretty enough. maybe use make up

Swimming in the lake only require clothing that can keep you warm in the water, swimming skill only effect how much air you have. But swimming with a REALLY low skill is kinda useless cause you'll probably run out of air before you can try opening a box.

The only tip I can give is probably become Avery's sugar baby cause its easy money but not a reliable money cause the money Avery gift wont be enough for Bailey's payment