The business income from the STR can be split on both returns or put through a partnership return and then to the individual returns depending on how you hold the property.

I recommend setting yourself up with other individuals in your area and try to use the same resources and vett or filter out the contractor that doesn’t meet your standards or business model. 

Either ripe the Band-Aid off now or pay tons interest and do it later. 

@Mel ParkI don't think your reserves for maintenance and Capex are at all realistic, I use 15% of gross rents for them combined but I've seen some people on here use 20%.That being said, it sounds like you're a high net worth individual so your aim is to diversify and not chase the largest return which is justifiable.

The theory is that if you own an individual asset in an individual LLC, your exposure to liability is limited to that individual asset, and a faulted party cannot come after any other assets, personal or business.

The tenant is just one individual.

If they are individual units, is it better for you to live there and give up your 2 story duplex?

Do I subcontract out all the individual skills or try to find a handyman that can accomplish a wider array of items (like outlets, lighting fixtures, exhaust fans, LVP flooring, etc.) and then hire subs for specialty items (roof, siding repair, painters, etc.)?

@Sean Barnebey you're really looking at two different individuals. 

I am a couple of counties south Hillsborough (Tampa) and in years past, my county attached the water bill to the individual and not the property, but they changed the law and it now attaches to the property.