If the real estate is producing a steady return, you can make more aggressive bets with stocks or other alt assets.

How much value would a web site with direct booking bring to this kind of arrangement as compared to listing on Furnished Finders, VRBO, etc, particularly if we stick with the mid terms.

Getting multiple contractors involved will be your best bet to get a reliable estimate, though you need to come up with a scope of work.

I also read in real estate by the numbers that it's risky to bet on market appreciation.

There is an app but it’s quite rudimentary so if you need anything detailed it’s better to just use the web version.

My son just joined the Navy and now that I’m an empty nester I want to make a shift and bet on myself!

Would not be a stretch to use AI or bots to do reverse image searches of your profile pics to scour the web for direct booking sites. 

If not, buying a turnkey, rent-ready property could be a better first bet.

@DeBret McGee IIYour best bet is to secure a deal with creative financing, seller financing or meter lease options.

I could maybe sign up with that theory if the GPs were using the side hustle money as a way of cutting or eliminating their fees & salaries altogether while they try to hang in long enough to hope for enough rate cuts to refinance or the market to unfreeze and let them unload at least at break-even, but I bet none of them do anything of the kind.