@Kyle Schwery Buying a property and providing a service are two different things.

@Jaime Pinedo let’s start with your price point, that will make all the difference in the world.

This negative cashflow, which I realize is fine for house hacking, could hurt my freedom to move long term as I would be forced to cover the difference from rent collection, however the question arises: Is it worth subsidizing $1400 in mortgage payments so that tenants can pay me $2200 once I move out?

We are in KS and serve a different niche and a slightly different model - but same all in all same type of operation as you -- we are licensed for 41 beds but really can only hold 34/35.  

Is this wise, or should I take a different strategy?

Then i would determine if there is a market difference in market areas.

There are many thousands of searches a month for that key term.Different Cities will have different competition levels for ranking.Diversification:Diversification applies beyond direct booking sites but you should have your listings everywhere.- VRBO- Booking.com- Airbnb- Google Travel (through Direct Booking Site)- Furnish Finder (Direct Booking Site)Speaking of Furnish Finder.

I'm looking into a few different options now: HELOC on other investment properties (though I'm finding rates are 11%-13%), a business loan on another business I own, and negotiating with vendors to take deferred payments. 

Cash offer do carry weight as they can close quicker, don't need appraisals etc, but as an agent that works with buyer and sellers, I've seen it many times where a seller will pick a different offer due to some connection to the buyer (ex military, young married couple just starting etc) They want to know its NOT going to an investor specifically. 

Realize your own experts may provide you guidance that leads to a different decision.In CA the LLC is $800/year.