Also do the escrow funds transfer at the sale of the property?

Philadelphia has the highest transfer tax have any major city I believe at 4.278%

Risk of him having a life changing event, with the property still in his name is another consideration, as to how it would transfer at time of death. 

That would give your tenants some assurance in transferring funds etc. which seems to be the goal.

The twist is that the dovetail method hides the transfer of real property because what gets transferred in the trust is "personal property" not real property.

LLC setup and deed transfer will cost you money though.

It’s my understanding that this warrants me to be liable for the title after the transfer rather than a quit claim deed which would not therefore terminating the policy.

The mortgage company that extended you credit wants their money once you have transferred the collateral to another person.Assuming you don't want to pay off your current loan with cash and then do owner-financing this really isn't an option for you.

He told me its fine and that i can just sign the property over to my LLC and pay the transfer tax.

Ithe wind warranty on Tamko is "Backed by a 30-year limited warranty, with 5 year Full Start, limited transferability, and a 60-month limited warranty against damage from wind up to 70 mph. ", but we do at least occassionally get winds at 70 mph.That's a lot of money to me.