Some investors want to know the sequence of questions to ask a prospect   I’ll never ask their name or house address until they qualify themselves as a prospect at the minimum amount of 85% of as is value. this is the first half of the qualifying script 1.

I dont do MLS listings so it helps me sort out the best qualified leads to send letters to.

I will only mention two critical points:- People with regular full-time W2 jobs cannot qualify for REPS (unless their no-W2 spouses can qualify)- REPS has nothing to do with STRs, and vice versa3.

@Tyler Speelman There's no issue if you want to convert your STR into your primary residence and live in it for those two years. you would qualify for a 121 exclusion which allows you to take the first $250k ($500k If married) of the gain tax free. 

If you're doing a 2nd mortgage on your primary residence to get the cash for down payment on the new Quad, then you're looking at needing to qualify with DTI unless you find a lender who is a DSCR lender and not a traditional conventional loan lender.  

Since you are an active service member the IRS will allow you to have lived in the property for two out of the previous ten years of owning it. you'd just want to verify with your accountant that you qualify for these extensions.Since you converted the property to investment, you may also take advantage of doing a 1031 exchange when you sell.

This might be a dumb question but would it be possible to use my significant other as my "roommate" to qualify for a house hack?

There are multiple ways to qualify for "material participation" but this would help to keep someone else under 100 hours. 

Legally, the GPs take on the liability of the project including things like signing on and qualifying for loans.

His "buyers" - who could not qualify for a loan because, presumably, they could not convince the bank they made enough to cover PITI payments - inevitably defaulted, and after a few months he would evict and start all over.