I have arranged financing in the event I want to pull the trigger (20% down).

She had a for sale by owner agreement (secret agreement) that she had arranged with the tenant that the tenant showed me.

It all depends on how much work he is doing to vet and find the properties and exactly what your arrangement is.If you are both finding and vetting properties and when you find one, he just puts his license number on it, then no he shouldn't get paid personally.Are you sharing all costs and work 50/50?

There is a "parking arrangement" where an Exchange Accommodation Titleholder (part of the Qualified Intermediary operation) will acquire and hold or "park" legal title to either the replacement property or relinquished property, and there is a concurrent/simultaneous 1031 Exchange. 

Also, unless you make arrangements otherwise, servicers such as FCI will not advance escrows.

Any tips or important things I should know about the application process and living arrangements etc. ?

It is usually based on the level of care and # of beds.I would steer away from renting directly to the person being cared for and have them make arrangements through the Assisted living facility.Your landlord policy might be slightly more as you are leasing to a business instead of individual renters.Hope that helps.

Essentially it ends at LL responsibility to "make repairs and arrangements necessary to put and keep the premises in as good condition as it by law or rental agreement should have been, at the commencement of the tenancy".

States have different laws about the occupancy of a unit to an owner and it's a little unclear on FL - but one thing to consider is cash for keys.To ‘sweeten the pot’ (and your timeline) you can also select a favored unit and offer cash for keys in which you’re basically are saying “here’s the notice of me not renewing your lease as outlined with x amount of days notice/can we come to agreeable terms to vacate sooner” so with an agreed upon arrangement of them vacating (get in writing)- especially if lease has outlined that it will continue with transfer of ownership and not near end date.

He has exercise equipment on his patio (very neatly arranged, he is a personal trainer and knows how to do this efficiently and safely).