Because of this estimated payment my debt to income ratio isn’t working out to push the conventional loan through.

I'm not sure what property values are in your area, but you may also be able to go the conventional route and put 20% down on a multi-family and not have the requirement of living on one side.

Your not going to get al of your questions answered but the goal is to start learning and building your network.PS I just got back from the BP convention in New Orleans.

In previous lending transactions I have had in the past, it seems like you just throw out an arbitrary number and the bank says yes or no , but the real answer I want to know is what's the most you'll give me and not push me over the conventional lending guidelines.

I would also consider using a convention loan instead of an FHA.

Any advice if I should go with an FHA loan or go the Conventional route.

For me personally, in addition to the extra protection the LLC provides, there is a law that prevents us from having more than 10 conventional mortgages under our personal names. 

Conventional would be better is it was just a single family primary home first then converted to rental. 

With a conventional loan the lender takes charge of doing all the services such as title search, title endorsements, etc. 

Otherwise you might be able to put 10-15% down conventional financing for another house hack and if you don't want to do that you could opt for a SFH with 3-5% down.