She also told me not to go with a "Big Bank" for my mortgage as this may be more complicated.

But when you have a three unit property, I would suspect that putting a tenant buyer in the property would be far more complicated because would probably need more than one unit filled in order to cash flow.

@Lafontant Cherilus lots of great advice stories here, but I just wanted to add that people have always told me things are too difficult/complicated/unattainable.

This is starting to seem really complicated but I want to get it done.I would love to get it set up to where I am paying the mortgage first and then him the difference.

I figure the three possible outcomes are 1) they both stay2) that she moves out, he stays3) they both move outPossible complication being that he stays, she moves out and he doesn't pay.  

You can establish a good business plan and run a rental property business without an LLC and it will be less complicated for you to do so.

Also let me recommend that if you do go the sump pump route, install it in the dry season as it is my experience that digging a new pit below the water table is ridiculously complicated.

Specifically, I'm looking for somebody with experience in entity setup/creation (I have a slightly complicated financing situation that will need to be managed to fund my REI business).  

For the most part, commercial seems a bit more complicated than flipping an SFR contract like this. 

Hello Maura,As long as your loan is presented and structure properly up front the UW should be able to figure out what you're doing quite quickly.In my opinion 60 - 90 days is unacceptable unless you have a really complicated file or the customer is really slow in getting the Loan Officer what they need.Find an LO that knows what they're doing and you should be able to get this done in less than 30 days 100% of the time.