What special purpose equipment do you have for an ADU/Office that required unique wiring for it to function? 

With Chicago's new Express Permit Program, it's a bit easier to get permits for work that would have previously required architectural drawings. 

If yu claim one it doesn't void the option to claim the other one.Provided you meet the IRS requirements for both, as a tax strategy, you could complete exclude a portion of capital gains under Section 121 and then defer the remaining capital gains under Section 1031 (@Dave Foster is a great resource for 1031 exchange). ..

This way they can't claim ignorance.I would also require a move out inspection and make it the day after they are supposed to be moved out. 

I don't know what his minimum liquidity requirements are to join.

Fix and Flip -Requires a minimum down payment of 10% with 100% of the rehab financed. 

Florida's treatment of security deposits varies from many states in that it is required that a security deposit be kept in its own account in a Florida bank.

Hard money lenders are much more like banks and come with many restrictions, requirements, due diligence, fees, etc.

It is pretty easy to keep it fully occupied but it does mean I turn away a ton of people who want a lease that doesn't quite fit my requirements. 

With your Fico and down payment, all you need to do is make sure you pass the debt to income requirements.