They both have some more strict STR regulations than I would be comfortable with.

If you’re not comfortable with your analysis and still want to pursue the purchase, I would recommend engaging the services of a real estate consultant holding the CRE designation and paying them for a short form report.   

I have comfort that their legal team checked off the necessary boxes. 

You would be violating the law for doing that.Be comforted that most prospective residents don't provide proper ESA documentation. 

If your PM is comfortable with it, then I would say its a good idea. 

Get out of your comfort zone.

(A figure >50 signifies a bullish/expansionary new home sales environment.)

They are very transparent about where the money goes and great stewards, of it so we feel comfortable giving knowing they're not using it for frivolous excesses. 

I believe it's actually a very good regulatory environment now that the permits are in place.Overall, I expect metrics to continue to improve over the next few years as the demand for STRs continues to grow in our market at a 15% year over year rate. 

High-dense urban environments should build up, and get rid of underutilized parking since public transit is easier in these environments.