I think my main pain point is underwriting the property as it is and then seeing what it could be and then making decisions on if it's worth and how those decisions are made.  

(Foundation, etc)4) Black mold, asbestos, lead paint, other other costly repairs. 5) It need significant cosmetic repairs where the purchase price just isn't worth it. 6) They may have an odd layout of the rooms. 7) Non-compliant septic.8) Trouble with permits or tenants9) Listing agent has a poor or incorrect listing.

I would suggest you do some soul searching before you make and decisions to sell.

They don't know how to properly qualify an investor.Check around before making a decision.

Your decision to lease this property for short periods is what makes this a short term rental property, not the property itself.

Maintenance hasn’t been too bad so far, and I recently made the decision to sell my business, so now I’ll be living off my rental income.My question is: What should my plan be from here?

Don't let tax implications drive investment decisions.

Evaluating the numbers, lending preferences, property condition, and location will help you make an informed decision that aligns with your investment goals.

Give sellers the space to make their decisions without rushing the process—trust takes time to build.Listen More, Talk Less: The best closers are the best listeners.

First, conducting thorough research and due diligence before making any investment decisions is crucial.