For most, a separate acct at your existing bank with a dba (so tenants don't pay you personally) would probably suffice. 

Having sold or refinanced the VA loan to release the VA loan from the property, your payoff letter that you receive from the bank after the sale or refi should suffice for this requirement.Lastly, why are you set on converting your properties to LLCs before they are paid off? 

Most garages are not built to suffice for livable space in their structure and foundation, so most of the time it will require a whole new foundation to be poured, and the structure is reinforced.

As for tools, being well rounded with excel and an account at Zillow should suffice for most things.

We flipped our primary residence (slowly) and our business partners have 2 rental properties -- I wonder if that will suffice. 

It does get complicated if you're doing it but if you're using a professional then just giving them accurate totals will be sufficent.

Can anyone recommend a Florida lease agreement geared toward an owner occupied property or would a standard contract suffice? 

I know there’s tons of information and or specifics left out that still need to considered for a more detailed response, but a general one will suffice. 

There's a much longer explanation for this that I won't get into, but suffice it to say it's inevitable.

I don’t know if you’d want to do a full rehab, but definitely fresh paint, repair any obvious things, carpet cleaning if that will suffice, or replace, clean outside…make it suitable for occupancy.