@Bob DoleWell, it seems like you have a very good grasp of the situation and the desired outcomes you are looking for.

The desire to buy something is getting too high as 2 years without a purchase is too long for me.  

Now, you don't dare take a chance on someone that shows any sign of being a risk.You've been sold down the river by politicians whose only desire is be re-elected. 

The Class system (A, B, C) can vary by market, but here's my general breakdown:Class A: High-end, desirable neighborhoods.

He has stated clearly to me that he does not desire to be a RE investor.  

What kinda gets me is when the same poster becomes hostile, argumentative, accusatory and or sarcastic because they’re not receiving the response they want (and probably just paid $5k + for knowledge/information/mentorship that won’t lead to their desired result). 

So the real answer is do what's comfortable for you and what makes sense based on your own financial position, your age, your desired outcome, and your local market.

Here's some STR companies in the area that can possibly help you out...Go Wander Home Desired StaysThe Sosi

No off-street parking = not worth doing MTR unless it meets all of the following: super urban area where no parking is the norm, highly desirable area with a ton of MTR demand, super safe part of the city, and has great public transportation (think NYC, Hoboken NJ, etc.)Unless it meets all of the criteria above, I pass on those opportunities because my MTR will be eliminating the many people that travel with their vehicles.

On the other hand, keeping the house could allow us to maintain an appreciating asset in a desirable location.I’d love to hear from others who’ve faced similar decisions.