I just got an escrow analysis from a new lender (transferred about a month ago) and there is an escrow shortage.

If you have enough stock that you don't need to sell all of it you could try to find a brokerage(you would have to transfer the stock to the brokerage)/bank willing to loan you money on the portfolio. 

. - Deed transfers to new LLC.- Current owner continues making monthly payments, we pay him after he shows he paid the mortgage on time.

Hi guys, so after I deeded a rental house into an LLC, lets say the LLC's name is  "ABC LLC " .... So now the insurance should be in the LLC's name?
On the insurance policy it should say that the insured is "ABC LLC"...

I am transferring their flood to myself as it’s assumable and I have multiple quotes for insurance.

Can transfering the title to a land trust help overcome the owner occupancy requirement on JADU

Thanks Yes, worrying about the due on sale clause is a valid concern, as it could potentially trigger the lender to call the loan due in full upon transferring the property into an LLC.

I have transferred properties into an LLC while I still have the mortgage.

This is because lenders are primarily concerned with the income-producing potential of the property when determining its value.In regards to your second question, it is possible to buy a property from yourself or transfer ownership between entities.

@Jason Carter I owned two B&Bs for years which provided a nice lifestyle and loads of skills none of which were transferable to a real life job situation.