I would then tell him that I think I have a good deal, but need someone with experience to look over my shoulder.  

There are lots of air-2-air heat pumps much further north than Chicago which work just fine - solo through the shoulder seasons and with an ancillary heating source in the dead of winter.  

I had absolutely no idea what I wanted to do with my life after I "retired" (shoulder and elbow were both giving out and I did not want to keep playing, making minimum wage, and go under the knife for both my elbow and shoulder) so I went back to college and got a couple college degrees.

True, it is unlikely you would suffer those for a single fraudulent HELOC application, but do you really want to be looking over your shoulder for years to come?"

Most importantly…do you have someone in your corner looking over your shoulder and giving you solid advice on a regular basis?

I also feel as though a weight has been lifted off my shoulders since this decision has been made, which leads me to believe that I made the right choice.

The potential is still there, and in an owner occupancy scenario rather than putting $800 extra into your rent account every month it is shouldering the burden of your housing cost.So, to evaluate your property, add up your total costs as mentioned above and then divide one months total market rent potential by that amount.  

My recommendation for an area with a greater amount of inventory would be Philadelphia, especially since the shoulder season is upon us. 

@David FantellWelcome to the site.Sounds like you have a good head on your shoulders.

You could do that by looking at bookings on AB/Vrbo and see what is available in a few months' time, in the shoulder season.