I'm leaning towards the rehab and rent ... unless the realtor brings us a "you can't refuse this" offer.There were multiple offers on the table when we went in, so we made an offer of $26K and sent a $15K deposit.  

You can deduct the cost and the time it takes from the security deposit

The owner of the home will most likely take the profit from that home and put down a deposit on a more expensive home, assuming the loan.

There is no deposit for one of my tenants.

In my experience depositing big checks, I've built and understand the "ego" that developed in myself.

My question is this....Would I have to put a deposit down on every wholesale that I do, being that I will be assigning the contract over to another investor?

If they are on a month to month lease, send them a thirty day notice to move out and keep their security deposit as past due rent for May. 

We did a 40-day feasibility period with a $5000 earnest money deposit.

They get $100k in deposits, use fractional reserve to make a $1m loan at 3%, then they get 30% of their deposits as interest.  

Personally I work above board, I avoid the "grey areas" as much as I can and play by the rules because I am not a fan of court rooms or depositions.