How much money an owner can recover if the bank take the property to an Auction? 

Without knowing what the loans would be from him, the interest rate, and the potential profit, it makes it difficult to really judge this agreement.However, based on everything but any potential loans now and in the future from him to you regarding the cars, I will give you the following analysis:1 - Your cost will be $150k (the cash DP).2 - Assuming no cars are involved, based on the projected yearly CF of $18k/year, it will take you over 4 years to reach the $75k in profit you will get before he takes any share of the profit.3 - After you get your initial $75k, you will be getting $37.5k (your half) in CF from then on. 4 - Since the first $75k recovered half of your $150k DP, and you will be getting half of that after that, it will then take you a bout 9 years to recover the other half of the $150k you paid in cash. 

It will say there if you just recover your money or have the right to sue for performance.

If the annual property management fee is $50,000, that could result in $10,000 of expense reimbursements the landlord will not recover.

Then you tell me if you barely escaped, or missed out.Recovery of Cost (Cash in) and start of Profit:A - Cash in = $40kB - Cash Flow/year (recovery):  $1,032/yrC - # of years until you recover Cash/Cost =  31 years (30 years of mortgage + 1 year without mortgage)It doesn't matter what the property value is, or where it goes up to, unless you plan on selling the property to get access to it. 

More than the security deposit, and far more than would be recovered by small claims court.

That's money that most senior citizens can't recover as their working lives are probably over. 

We are all ok financially and would be able to recover if we lost the full 100k. 

Wanted to take advantage of the small/tiny home niche in Houston and provide local and traveling people (nurses etc) a place to recover and relax for a day or two.

@Hugo Jimenez this is definitely not something that comes up very regularly; however, it is specifically addressed by Florida State Statute 83.59(3d) as indicated below:F.S.S - 83.59 Right of action for possession- (3) The landlord shall not recover possession of a dwelling unit except:(d) When the last remaining tenant of a dwelling unit is deceased, personal property remains on the premises, rent is unpaid, at least 60 days have elapsed following the date of death, and the landlord has not been notified in writing of the existence of a probate estate or of the name and address of a personal representative.