This is sooner than we expected but the opportunity arrived so I would like to take advantage of the extra income.

I tell my wife all the time “man, I wish we would have started this process sooner!”

We are looking to have some consulting conversations with experienced and knowledgeable advice for how we might best build up our cash flow so we can use our wealth to retire sooner.

Our friend from the gym is buying a new house, which is contingent on them selling their current house.

It's not like you can invest the same money in multiple places, and it's additionally very rare that you can get an immediate payout on an investment, so why would we discount future money by the rate of return, when there seems to be no reasonable scenario where we could actually have that money today, or any sooner at all?

However, I ideally would like the displaced tenant to get back on their feet sooner, so anything I can do to help...4.

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.

I would frame it as telling the seller hey I may get your balloon earlier than the agreed upon rate, would it be a problem for me to get your money back sooner than that? 

The sooner you do that the sooner you will get that Section 8 money rolling in. 

For your own closure the sooner you give it back the better.