I THINK he changes his taxes from regular income tax plus self employment tax down to just capital gains if he holds beyond 12 months, but even that may not be true.

About 1/3 of our current tenants pay regularly and on time.

Are you happy with the regular base algorithm, or do you make a lot of adjustments and changes?

As an industrial real estate agent, I have clients do this regularly.

I would self manage...in a way..I have a crew I use pretty regular for all the rehabs I do so I have people in place to help if I go the STR direction.

Did you buy the paint for the painter who is doing side work from his regular gig... probably your employee now as far as the state is concerned. 

What you've listed as work is really nothing that a "regular" homeowner would do to their own home, even potentially at the same time. 

If a tenant is regularly late on payments, there is a very high probability that they will eventually stop paying or violate the lease in other ways that cost you far more than the late fees you see as "extra income."

Not that regular rentals are getting any easier, but there is not a massive push to shut them down via regulations.

One way to do this very inexpensively is with a combination 6-20 and 5-15 plug: This uses very low cost wire and is basically a regular outlet except with 220V available for those with a matching EV travel charging cord.