It is distressing to realize that as I retire I will not be eligible to use the bank to buy my next home.

About 5 years ago we hopped in a RE syndication and pulled out of it recently to take a more active role in our investing (returns where meh), along with trying to supercharge our financial goals in retiring early. 

I built a solid retirement portfolio from SFHs with added value. 

I don't think I will ever fully retire but I plan to be doing less active work in the future, i.e. not focusing on writing new loans and not flipping.I am lucky that I can easily handle a down turn and be just fine if things soften even for an extended time but I still hope that doesn't happen.

Your goal is to create an income producing portfolio so that you can retire from your blue collar job in 10 years.   

Property is exempt from STR permitting because the jurisdiction considers it to be a commercial lodging establishment.We've been pursuing an SBA 504 loan for it, which was going well until we discovered that the sellers have operated it only part-time the last 12 years -- intentionally blocking 60% of available room-nights because they just weren't up for running it full time in their retirement. 

Equity and retirement assets wont do anything for DTI unless youre retirement age, have a plan in place to create income via IRA distributions, and have a sufficient balance for the distributions to continue for at least three years. 

My question is how will a house sale affect his retirement and selling me the house at a discount will affect me?

Your goal is to create an income producing portfolio so that you can retire from your blue collar job in 10 years.

Investors see headlines in the WSJ or Bloomberg talking about syndications loosing money and investors having significant parts of their retirements wiped out and more news that most of the short term debts mentioned above are expiring end of this year and early next, making it seem like the worst has not yet come.3.