Hard money isn’t cheap, so bridging that with a seller carry might help you short-term, from what I’ve heared.

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.

I imagine this isn't cheap but I don't see another way.

Add thoughtful touches like a Keurig or French press, USB chargers, and local travel guides.

Got back from traveling. 

Combining short term rentals and a venue is a huge advantage because guests would not have to travel far and you could offer better rates as part of a event package.My current venue focuses more on baby showers, content creation and birthday celebrations rentals.

To me STR and hotel caters to different groups of travelers and so despite competition as long as the travel demand of Hawaii remains (as you pointed out is a robust assumption) I think both will continue to do well.  

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.

My agent is currently finding best rates with Travelers.   

He currently travels often for work and resides in TN.