Whoever does, will be a punching bag for the rest as prices are NEVER low enough for owners.Who's going to get the proper license(s)?

@Kenton Guidry I am a licensed Realtor in Tyler.

Homeowners are going to be required now to actually verify licenses, which isn't hard at all to do. 

BP helped me to establish myself as an investor and I decided to go all in and got WA Real Estate license. 

You can arbitrage as long as you have your Vacation lodging services license, but finding an owner to let you Airbnb their property is very hard to come by.  

Now that my wife and I are looking to buy a primary home in a HCOL city, I am considering representing us as an agent since I hold a license here.

I am a licensed local property manager in the greater Asheville NC area and looking to  locate PM's in the area who may be looking to retire from the business and sell their book of business. 

That said, I would strongly advise that you get a lawyer involved, or at a minimum a licensed Realtor (you mention "brokering" the deal, and that you are a SWE for Google, but not that you are a licensed Realtor...if you are then disregard that last part).

A Business License is required to operate a short-term rental."

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