Depends bro, usually I end up buying around 6 upgrades until the second week, I also spend the morning ramping my stamina, and in evening I only make it 1 minutes cuz that's about what I can do. Jogging Grind also helps with money, textbooks to upgrade your stats, and so on.
Better yet, try as much as possible to micromanage your tasks well, only post a vid once per two days, everyday filming would burn you out.
As for the clothes, check the top of the drawer, the bras are usually going there too if you made her topless. As for Pajamas, just by the side of the bed.