I'd say just start your search with all 2-4 unit properties, and when you find one where the numbers make sense and it checks your other boxes (somewhere you actually want to live and house hack), then it probably makes sense. 

By this logic investing in a new roof also doesn't make sense.

People get stuck on "this is my bottom dollar rent" and shoot themselves in the foot refusing to make adjustments. 

My niece spent 12k learning to apply make up and be a make up artist.  

Utilizing the preREO strategy, a receiver (i.e. a local real estate agent or property manager who you may already have a relationship with) could be appointed to make repairs and rent out the home during the foreclosure process.

Nights, weekends, holidays, etc.To keep this on-topic, though...DO figure out what's healthy for you to manage but remember it's a process where every experience teaches you good and bad (and be patient with that process).DON'T sweat the small stuff (damage/costs under $50, undisclosed dogs, etc.) but DO find a way to learn, prevent, put in better practices to maintain your sanity. 

The general rule of thumb when using debt is to ensure that whatever asset you buy with the debt should make more than the debt service.  

You'll definitely need more time to get things processed.

Makes the wipe-off work for nearly everything.

When starting out in wholesaling real estate, it's important to use agreements that protect all parties involved while ensuring a smooth transaction process.