First step would be connect with a local lender familiar with the strategy specifically utilizing fha loans.

It takes reps and reps to do, and generally having a commercial specific calculator for the assets you are looking at would be helpful. 

This is a pretty broad question and the answer is always going to be very area specific.

Year of update of the systems (roof, plumbing, electric, heat)4. any pets, pools, tranpolines, or business use at any locationThey will usually need more specifics but this is a good start. 

Jumbo Loan What was the outcome?

Both companies suck but do have impressive customer service outcomes from recent complaints.  

I can provide you with some specific examples and illustrations if that helps.  

or the split model where guest pays part of that …Anyone have specific experience on these two issues?

Here's my advice: Section 8 isn't inherently good or bad; it depends on your comfort with risks, your experience level, and the specific property.

W-2 determination isn't a choice to make, rather an outcome based on the facts and circumstances.