If you are not going to leave there at all, and you can't do Bill 23 or have any value-add to get to positive cash flow, then NO, don't do it. 

Values go up, tenants pay down the mortgage, you refi, and keep buying.Don't over analyze looking for the perfect deal. 

Building a sport court will run like $30 grand, but would increase your rental value. a 6bedroom 4 bath house with a sport court, hot tub, fire pit, mini golf, arcade etc. will most likely crush it because it's cool.

Without major rent increases, multi-family property values tend to stay flat.

I just realized that section8 and forcing the value in a home "FOR RIGHT NOW" is not for me.

Living out of state, I accepted the photos she sent at face value.

Then in the slow season we are at $119/night and people complain about the value and little ticky tack things that no one complains about above $200/night.  

It is incorrect, but it will also lower your value!

I assume cut value by 20%?

I would consider selling if you have lived in the home the past 2 / 5 years since you have a decent amount of tax free equity in there but as long as you have a plan to reinvest those funds.By your numbers, since you have an amazing rate and high rents, I would consider renting it out if you believe your area will continue to grow in value.