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

transfer or foreign filing?

My main two questions are: How would we structure ownership of this property?

You can also look in areas like Roland Park, which is also really nice, but you won't find many renters there, as that has a very high ownership rate. 

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. 

In all of those cases the tax payer remains the same because the tax return reporting the properties stays the same.That not only simplifies ownership but also lending as well.

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.