A quick look at VRBO shows over 300+ listings so there is competition.

Ive been told to build a huge buyers list to just get it under contract and market it.

Do you have a list of recommended lenders?

What's left is simply $ to close (HML easily solves that) getting the vendors to do the "simple stuff" (pick your platform; Angie, Neighborly etc etc) and than to sell it (more agents than one can count happy to list). 

It's worth the $250.You have a pretty broad and "standard" list of items that you would inspect for sure!

Narrow the list down then, last step is make the time and go tour them. 

I immediately got home and created a laminated note about the unique local bakery, which bakes the best croissant I have ever tasted, including the croissant I had in Paris, just around the corner of the Airbnb listing.

Run credit and background checks, actually call the listed referrals, and ask for bank statements.

I will be listing for $495,900.

Obviously the answer is yes when it comes down to the cash flow, but I am particularly wondering if HCOL/high property tax areas are places you would cross off the list entirely.