You may be able to capitalize on this if your area has experienced similar growth.Simplification: Selling would allow you to focus on your new single-family investment properties and potentially expand in those markets.Capital for other investments: The proceeds from selling could be used to fund other potentially higher-yielding investments, especially if you use a 1031 exchange.Small town limitations: Depending on the specific town, there may be limited growth potential compared to larger markets or more popular tourist destinations.Given the stable cash flow, low remaining debt, and your established experience with the property, keeping the fourplex seems like a solid option, especially if it's in a location with STR potential.

Is fixing and flipping in Charleston, SC popular?

I'm seeing parts of Durham become increasingly popular like 27703 for new construction in addition to Bethesda and South Durham near Southpoint Mall. 

Second In-N-Out Burger Coming to the Strip: The popular burger chain, In-N-Out, is opening a second location on the Las Vegas Strip at the new BLVD development, across from City Center.

I know Craigslist is very popular for renters and landlords in SF so I assume the same would be true with Berkley.

Many hosts find a Fri-Fri or Sat-Sat strategy works best to maximize bookings since families often prefer a full week vacation, and it aligns with popular check-in/out days.

Bird dogging may have been more popular before the internet, google maps, etc.

Hartford is a popular market with a lot of agents, lenders, and local investors.

The cape is popular and growing.

While I do think that extreme climate is something we all will have to contend with, I think the area will always be popular as a vacation destination.Having said this, I am thinking about looking for a STR in the area.