Strange twist... gave her a call to ask if she was able to send docs to show actual numbers by the end of the day and she explained that tenants are not on lease agreements but rather hand shake month to month understandings.

If you are asking if one strategy is riskier than the other then  the answer is mine is but thats only because of diversification alone.I think what you are asking is  what is the  riskier strategy. the only time my strategy would benefit me and hurt him is if the banks start having problems. for example if the bank calls the loan due for some strange reason he would be in trouble as opposed to me where I dont have a lender. 

Somethings seems very strange here.

It is a strangely worded and vague contingency clause.

Strike two.You (for some strange reason) want to "do right" by them.

Fifth Third Bancorp, just strange having no communication from them.

if people would put as much energy into making themselves financeable, as they do making up strange one off, highbred, creative deal, smoke and mirror, hide the note structuring, the world would be a better place...IMHO.

This place is weird, fundamentally strange in its own peculiar way.

On top of this, he is asking for 1 months rent and the deposit (also 1 mo rent).I feel very strange about paying rent and deposit without even having a move in date. 

He volunteered this information to me after I said it was strange that these foreclosures which had been on the market for over six months suddenly had multiple offers.