I am in the Tampa bay area now but grew up in Kentucky and travelled to Indy many times!! 

Examples might include areas in the Midwest, Southeast, or Sunbelt regions.Multifamily Properties: Consider duplexes, triplexes, or small apartment buildings to increase unit count and spread risk across multiple tenants.Short-Term Rentals: If you’re comfortable with the management requirements, STRs in vacation or business travel markets can offer significantly higher cash flow potential than traditional rentals.Value-Add Properties: Look for opportunities to buy undervalued properties where you can force appreciation through renovations or better management.Decision FrameworkRun the Numbers: Compare the projected cash flow, equity growth, and tax implications of selling versus holding with a refinance or HELOC.

It’s amazing to see how much the market has changed since then..and I remeber reading an article in Forbes that talked about how travelers often prefer unique stays with great locations.A friend of mine up in Lakewood had a client who tried an Airbnb in a condo overlooking Sloan’s Lake.

Since our residents are traveling "light" to a furnished property, their coverage only costs a few bucks per month. 

While I use it primarily for noise concerns (it alerts me for sustained +80 decibels), it's also handy for cigarette smoke and tracking temperatures (in addition to our Ecobee thermostat)- sensors on all exterior doors and possibly windows (which you might have via smart locks for the doors)- exterior camsA recent guest for reasons only known to them set the thermostat to cool and 60F in the winter (where it's currently a balmy 11F). 

My answer would certainly be highly dependent on his own emotional make up, his desire to relax and travel, his willingness to delegate and outsource, etc.

@Jon Latorre I'm traveling to CR next week.

Be aware of tax implications: rental income is taxed in the property’s state and reported on your California return, with deductions for travel, depreciation, and expenses.

So Keep your property but don't mid-term unless it is very small house and would appeal to traveling nurses on 3 month gigs.

INstead of just saying "no" we asked them to check with their credit card company if they offer travel insurance yada yada.. we got a 5 star review form them without giving a refund.