You can't completely remove emotion from it, but how much would it cost you to hold it and what could you get for rent? 

It was my first step into real estate, and I got screwed with repairs that were never made, and lead paint removal.

I'd let him use removable wallpaper if he wanted to buy it.

I'm also pretty confident that Airbnb is becoming more aggressive and would remove an unfair review.

I would recommend selling on a land contract so you don't have to sign over the deed to the house until the buyer pays off the note- You get to help someone buy a home when they wouldn't normally qualify- High interest rates means you may be able to lock in really attractive terms for your buyerLease Option- Lease out the property to a tenant who gives you an option fee upfront with a future purchase price- Tenant will pay above market rent and it becomes like a NNN situation, you are very removed as the landlord.- If the property needs work, it's the tenant's opportunity to build sweat equity in their future home- If the tenant does not execute the option, you get to re-lease the property to another lease option tenant- If and when you do sell to the tenant-buyer, you avoid the traditional home selling process and associated closing costsHope that's helpful for you @Edward Giyo

However if your are going to paint and do floors, remove floors then paint, install new flooring.

Long-distance Landlords typically let properties deteriorate or allow bad tenants to damage a community.A good PM watches your property, inspects the interior regularly, choose solid renters, removes bad renters quickly and efficiently, reduces vacancy, handles maintenance quickly, keeps your property at market rates, stays current on the laws, and much more.

I'd consult local attorneys to see what costs would be associated with removing a tenant in your state.

In the event that it looks vacant, I close, and the squatter breaks back in (while I’m at work or having it tented for termites, etc) and claims they live there, how do I ensure that I have the right documentation where I can call the police to take care of removing them?

You are complicating the "cash flow" scenario as you are adding a HELOC payment on top of it as well, so you'll need to take that into account. and you may want to think about something with value add potential so you can hopefully refinance and pay off that HELOC in the next year or two, as well as refinancing out of the FHA loan to remove PMI.