Beachfront or properties near attractions tend to perform best.Mid-Term Rentals (MTRs): These are gaining traction, especially with traveling nurses and remote workers.

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

Since you plan to travel often, focusing on systems and building a reliable team: agent, lender, property manager, and contractor. 

I have been travelling.

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.

I would be amazed, shocked even, if a traditional financial institution was willing to lend on a non-habitable asset up to 80%. 

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.

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

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.

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