Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

These are the kinds of questions business and tax planning would help you to explore, think about, and answer.

We have explored disposing of the asset multiple times and the same comes up during sale.  

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

I'm surprised someone verbally told you you can convert back to a duplex and didn't tell you that you must get permits.from what you are describing it seems the town gave you a hard time because you didn't get permits, I don't know that you have any legal standing to go after the town,  again, I am not an attorney 

Quote from @Michael Smythe: @Kwanza P.Recommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

It’s worth exploring to see if it aligns with your investment strategy and timeline.

Each week, I analyze the MLS, exploring cities and towns across South Florida to identify areas favorable (or not) to short-term rentals.

Any underrated markets worth exploring?

If that's my experience in a small town, I suspect it's probably everywhere.