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

Assuming you don't have a mortgage that requires a certain level of insurance, you can get a stop-loss policy covering all the properties. 

We lend up to 85% of the build costs but, generally, require that our borrowers have some experience with ground-up construction. 

typically no special license is needed when doing it for hard money loans that I am aware of. there may be states like california and nevada that are tricky where lenders need a license of some sort but for most part brokers i have seen are not licensed. 14 or 15 states require state license and NMLS registration.

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

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

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. 

There is still money down required but helps ease costs

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.