I've negotiated a lot of short sales as an agent.  

I get 2.5 points charged with each one of the two loans, I have no leverage to negotiate the 30Y mortgage rate, no closing credits and if I want to refinance with another lender in the market I'm charged a hefty fee that will make the other loan unattractive anyways.

I started out as an agent negotiating short sales, so I know the good the bad and the ugly on those. 

I would try to negotiate those terms ( and you can) full months rent seams like quite a bit.

Banks don't typically negotiate either.  

Then you sign a lease and negotiate a rent  amount. 

Since I write for a national title insurance company, if he wants a buyers title insurance policy I would get him one ( and the seller/mortgage holder as well)Oh yeah if he needs an offer or  P & S negotiated I would do that too.All just in a days works for a closing attorney here in MA!

Your on the right path finding a good deal is important but even more important is negotiating the price and terms.I want to help you I have a list of homes in central florida and we can l want them and pick the ones that fit your needs and wants lets connect and I will give you the details. 

Made an $8,000 offer, and they accepted with no negotiation.  

The one in Lakeland, FL that turned a ghetto house into $1500 cash in my pocket, the call from Kissimmee, FL that has a $10-25k flip potential, and one message asking to take their name off the list (which is better for me because I don't want to spend anymore money marketing to people who have 0% response rate anyways).Just be light and conversational to your sellers and buyersYou make your money on both ends of the deal, so negotiate the heck out of your seller's price (but be respectful and don't risk losing it) and use a realtor to give you true competitive comps on your sales price so you have supportive evidence for your price and cant get haggled too far down by your buyers, because they will try.Every cash buyer on my list wants their deals to be acquired at 70% of market value, including purchase and rehab.