Just step into a buyer's shoes.

You simply give the homeowner cash and then step into her shoes to be foreclosed on. 

If he is an old investor, he can likely relate to being in your shoes, I would work on rapportWith the seller, get to know him better ( go get lunch or coffee.)

OOS investing is definitely an option, and probably the one I would go with if I were in your shoes.

That would be my first priority if I was in your shoes.

If I were in your shoes, I would invest elsewhere (I essentially have, I rent on the UES and invest in upstate NY.) 

Everyone here has been in your shoes.

If I were in your shoes I would figure out how much the down payments will be on 4 properties, refinance for half of that amount and then take out a Home Equity Line of Credit for the other half. 

One quick opinion from you - with the way the Orlando market looks, if you were in my shoes would you prefer to invest in a small multi-family, or a single family like a 3/2+ and rent out rooms individually?  

I am in your shoes.