If you can prove to a lender by some other source of income that you can make a monthly payment you have better chances of procuring that loan. 

You may also want to look into comps for renting by the room to see if that could procure more cash flow?

As long as the conventional loan assumes the FHA on your refi there shouldn't be an issue procuring a second FHA loan.

Its important to not do any work on the property before you receive the title, this is because the owner can file an objection and pay the amount owed in full.It can be intimidating and difficult but also an amazing way to procure a good deal.

Before I get to my question, here is some financial data for me in June 2021, on the first day of retirement:Monthly PITI for 7 Properties:                      $15,485Rent for 1 lease-to-own property:               $1,643TOTAL PITI and RENT:                                 $17,128-Monthly Rent collected from tenants:         $32,225-Income from Summer truck driving  job which I will keep doing for a few years: $2,000 ($24,000 averaged over 12 months                                                                         TOTAL INCOME: $34,225Summary: Incoming cash is almost exactly TWICE my PITICredit score: 820sSo here's the question: (on a scale of 1 to 10) how likely am I to procure financing on additional properties after retirement?

If you're not "assisting in procuring a tenant", but merely checking the security of the property on a regular basis per your written agreement with the owner and the owner schedules the prospect at at time when you're at the property anyway, you "should" be safe as long as you don't discuss the property amenities or lease terms.

Anyway, I recently realized that if I don't get moving on procuring investment properties that it'll never happen...I'm a homeowner in the Denver metro area (Littleton/Morrison specifically), and after analyzing a few handfuls of properties I'm thinking that I'll probably start looking at markets outside of the Denver area for my first few deals.

. , @Todd Rasmussen , @Greg Powers , @Bjorn AhlbladHere is what I was able to procure.

The fact that they required it, makes them seem like an amateur operation (at best).You implied that they were using your own credit history to procure the loan rather than that of the sponsor...which is a huge red flag if true.  

This will likely end up before the gcaar grievance committee with a procuring cause claim, which could prolong this from closing even longer.