Recently, the inspector was over 20 minutes late, we had to pull our Team Member to a different property, and the government agent could not comprehend why we could not afford to have an agent camped at a property indefinitely.

We need some help with a strategic plan- I assume we wouldn't be able to afford to buy more rental properties while buying a new place for ourselves.

. - Market:  Demand is high for affordable housing and my rents are below market, for now. 

I'm wondering if it is more affordable to tear down a dilapidated mountain home and recycle its foundation and utilities, rather than buy a plot of land and develop it.

If that's the case then there is your answer right there.It seems like most things are leaning you towards selling it if you are worried about being able to afford any unwanted repairs or capital expenditures, and if selling it allows you to get into a nice new house hack (if that's where you go) then you can live for free or at least cut your living expense way down.

I am working with a guy that is looking to get out of his restaurant/banquet hall due to age and impending health concerns. 

If the Tenant refuses to participate then that demonstrates they are not subject to the protections afforded renters that were impacted by COVID.

I had a lot of friends at that time that were more than happy to rent a room in a house at an affordable rate.

If that was the case, there is no way I could financially afford to go the section 8 housing route. 

@Patrick Thomas DickinsonYou’ll find affordable homes in the Midwest and may be able to get a few small multi family and have a property manager manage them.