It's not uncommon for Class A rentals to negative cashflow for the first 3-5 years, until rents increase at a higher rate than taxes & insurance increase.While this can be an unpleasant situation, Class A properties tend to appreciate the most and attract the best/easiest tenants.

If they are below market rent, that is OK as long as there is room for improvement and tenants won't be an issue.

Splitting utilities may be an issue in this situation.

It may be frustrating but check your state and local landlord tenant laws regarding this because it could be an expensive lesson for you if they’ve followed required procedures.

My goal was to be an entrpreneur, never go to school or join the military and definitely not work a 9-5. 

I don't want to be an idiot and spend it all away.

So this could be an area that is just more attractive to longer term tenants?

I have a colleague who specializes in the Yosemite market on STR, not sure if that would be an area of interest for you.

Suburban sprawl: everyone wants walkable neighborhoods with a coffee shop at the corner, but we have a monoculture of single family homes to the horizon5.)

Likely the DSCR wont be an option.