I'd encourage another house hack or a live in flip.

Should it be encouraged or frowned upon?

Be responsive to inquiries and provide detailed check-in/check-out instructions.Online Reviews: Encourage satisfied guests to leave reviews.

If you have (2) free and clear rentals with no mortgages I would also encourage you to pull cash out of them while values are in favor of cash out.I would avoid a Heloc and just do a cash out refinance the rates are lower and the terms are longer so you get a lower payment.

In this day of housing shortages and rising rents, you mentioned you don’t want to deal with all the “Covid19 no eviction garbage,” yet you’re ok creating a facility specifically designed to encourage others to congregate during a pandemic? 

So I would encourage you to just consider your "motive" with that comment. 

I'd encourage you to try to find the unassuming guy that drives an old truck/car, buys his clothes at Costco, and never brags about how many properties he owns.I'm just a small time landlord but I'd be happy to help if you think that I can be a resource.

It is great to slowly have cities that do 1033, in order to establish a proof of principle of how this law can work, and encourage other cities to follow suit.

While not explicit, the contract is written in such a way to encourage a commission, and discourage an hourly pay structure.   

However, I would encourage you to finish up your current loan before doing anything.