You've possibly stated in writing that you (may have) violated several laws ie. working as a property manager w/o the proper licenses etc. 2.

After weighting all of that, does it make the most sense to try to keep this tenant in place? 

Although the forum input can be helpful, you need to have proper legal precautions in place rather than opinion.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

But again, there is a charm to older properties, because if they do have the proper envelope a great structure, and the ability for a functional layout, they can have a lot of potential. likely a full gut...

Not every lot will allow you to STR even though sevier county and the city propers do have specific zoning that allows it so you don't have to worry about them ever rescinding that right. 

@Kyle Carter we manage around 700 doors, with 92 of them being S8.When S8 applicants are properly screened, they can statistically perform a decent amount better than cash-tenants.

In fact if you don't do proper due diligence some are "traps" with bad layouts, fire damage, and tiny sized lots. 

Have you ever had a year where your insurance or proper tax’s went down?

Since flips are typically treated as dealer properties, profits are taxed as ordinary income.Please make sure your entire structure is properly analyzed for you to save most amount of taxes.