Thankfully I was able to sell both houses and stop the bleeding.During the sale process I found out than one of my houses had a baseball sized whole in the roof and the other had two AC units that were not functioning along with mold that had to be remediated.

Fines are steep if you are found to be in violation. 

Is there a defined definintion of occupany that mandates a set amount of days per month that I must sleep under the roof of my primary residence?

Got insurance involved and use that money to remodel the entire inside, and add a new roof.

So some things will be easier and more convenient (one roof to repair) but many tasks will simply be a multiple based on the number of doors.

Outside we had trees taken down that were going to cause major future problems with the roof, gutters and the view.

I’ll also amortize large items like roof over 20 yrs, and then add $100/mo/unit for general repairs.

I'm not how you are defining a BRRR that works, but if I have a unit with brand new roof, mechanicals, kitchens, bathrooms, etc... and leave 10,15 or 20% in the deal I still feel like I'm winning.  

Lets say you needed $100k in financing at 12% + 2 points and it took you a year to rehab and refinance that is an extra $14k + closing costs.2. you mention roof is 18-20k.

I recently paid someone to do my roof and replace the carpet (~5k expense) on my short term rental in 2023, however he won't fill out the 1099-NEC.