Typically the HOA fees are too high and eat all your profits. 

Such as in a resort where renters can go and eat, pool, drink, etc.

Very often I meet real estate investors who chose to go with a $200 tax return filing accountant who costed them thousands and tens of thousands of dollars in mistakes like miscalculated depreciation, missed deductions, miscalculation of capital gains when selling the property and so on.I understand you don't want accounting fees to eat all of your profits, but I simply encourage to factor what you're getting from your accountant, weigh it against the price and find the combination that works for you.

(As in I get no reservations when I have them, so I eat the cost of cleaning and make almost no money for a 1 night stay which is a very frequent reservation request.)

I recently heard of a conference with top real estate executives that had a panel of 5 millennials.The millennials sat on stage and these executives asked them questions about where they eat, what they do at night, where they want to live, etc.How often is everyone taking millennial activity into account when making investments?

The DSM Metro does a nice job of keeping clean and hosting multiple "touristy" events annually... for which the locals EAT UP.   

Stainless kitchen with peninsula doubling as an eating bar.

But this industry will literally eat you alive.

(nothing on paper yet)or do I eat my mistake (property will still make money) but I am now in the hole an additional 20k to start?

But a fat  wad of greasy twenties stinking of sin...I'm just a man, Cody.