At what point should I consider transferring ownership to an LLC?

1110 E De La Guerra St looks like a fun one that was just listed :-). 

transfer or foreign filing?

You could close and then transfer it into an LLC however, you could run into a problem with Due on Sale Clause unless you are in a Fannie Mae Loan.

A quick Google search and I found out buying on land contract has these disadvantages because title was never fully transfer from seller to me until once contract paid in full ( great lesson for me) Those judgments from an insurance company are about $20k more than what I owe him.

the documentation and transfer of funds. 

My mortgage broker recently told me that they know a lender who allows clients to transfer rental property title to LLC, but keep the mortgage under personal name. 

I told them I wanted to put my rentals in an llcthis person does happen to be an agent, they just seemed like they didn't really know what I was talking about I just want to make sure I'm doing things the right way I don't hear people talking about having physical office spaces.. my llc is created already and in the process of transferring property 

Keep in mind you can always transfer a property to a LLC later.

I highly doubt a lease is terminated upon receipt of such a notice as title does not transfer.