The only two issues I have with going full time in RE is finding affordable health insurance and traditional bank financing is at least another year out before I can qualify for it.

And, I know that poking a bear in the face is bad for your health.

https://www.courier-journal.com/story/news/2020/01/23/university-louisville-health-hire-nearly-400-nurses-and-doctors/4534848002/Always great to have an influx of jobs, especially high paying jobs and better healthcare of course. 

If you convince him about the long term health of your shop he could cut you a break on rent for the next few years and have it grow a few basis points above inflation once you have your feet under you. 

The only way I see you being denied is if the property does not pass the physical inspection, which simply requires a clean home with no safety or health risks.

Has the health department approved of the plan and equipment? 

The best way to price your listing effectively is to look up other comparable Airbnb/VRBO listings in our OBX market (size, bedrooms/sleeping capacity, bathrooms, town/neighborhood, proximity to beach/sound, pool/spa, amenities, elevator, etc) and price your property with competitive/similar pricing. 

I'm getting a HELOC on a paid off vacation home I 50/50 co-own with an elderly, health-compromised relative whose credit is MUCH better than mine currently and plan to use the proceeds to completely pay off higher interest debt as well as acquire my first property or two.

They also informed me that they had to go to urgent care because they couldn't walk on their foot and didn't have health insurance.

You said it best, trust is a two way street and may I add, we all need to trust each other a bit until there is reason not to, if maybe even only for the sake of our mental health (not healthy to live that paranoid all the time over everything).