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

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. 

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.

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. 

Indianapolis has proven to be a stable market with great returns, without the boom/bust cycle you've seen in other areas.I'd love to discuss how our properties can fit into your investment strategy and help you achieve your goals.

However, I understand that achieving these goals is a gradual process—one that requires patience, diligence, and a stable foundation.The allure of “financial freedom” and “passive income” often captivates new investors.

Maybe, instead of saving for a house, you save for a job change, whether it will cover your expenses for a few months, while you work a much more flexible job, and look for better additional work, or get training for a job that is more stable. 

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.

I experienced the same through Rent to Retirement. 

To anyone raising money, there is nothing more sacred than other people trusting you with their hard earned funds and retirement money.