@Khandbari Rai pros- you can make a  smaller  payment ( the Int ony  payment ) for  up to 10 yrs    ...cons - the rate for this program is slightly higher than regular amortizing loan ...if you make the min payment - your loan balance  will not move  down at all  over  10 yrs  -  the lender  uses the  full amortizing  payment for qualifying  ...at the end of 10 yrs - the lender will change the payment to a  fully amortizing payment for the  remaining balance over the  remainder of the loan term ( likely to be 20 yrs)

A regular mortgage for purchase then a creative loan for the reno?

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?

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.

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

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. 

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