We currently have roof done and siding up. 

Especially as i have aged i find hot weather less pleasant. 

I assume the PM side (we use the investment management arm).They have to do their due diligence to make sure you are who you say you are.

I an afford to sit on this property as its in the Yosemite AirBnb hot spot and don't need to do anything right away as its in a killer location.

Just to confirm my understanding, you are living in a side by side duplex in Miami - you want to renovate the other side that you aren't living with a renovation loan?

One quoted $20k to put piers on 3 sides of the home, and another quoted $10k to put piers on one side. 

I'm a local Baltimore realtor and I know for a fact that this market is red-hot and everything, and I mean anything, can be sold for the right price.

So if he were to rent it out wouldn’t that show up on his taxes and say if the bank finds out and is okay with what would he do with it on the tax side of things would he report it as soon as it it’s in service or what would he do for tax purposes.

I'm a pretty big advocate for the south side of chicago where you can find properties half that value and cashflow really really well in turnkey condition. 

From the little I know of San Antonio (I am a wholesaler who specializing in selling STRs nationwide) its not a super hot Airbnb market but the amount you expect for rent sounds pretty conservative.