Got to get these men boat parking lol.  

To be more specific about what i'm looking to do: My 1-2 year goal is to employ the BRRRR strategy with SFHs and Condos by buying distressed / highly undervalued properties that need work (preferably all-cash) in low crime areas with strong rental demand, renovate them within budget (again preferably all-cash) and get them rent ready before refinancing them at the highest ARV possible.

Please note that if the Board does approve your request for a special exception, you will need to get a new Special Exception every three years when you renew your STR permit."

I get it...I get emotional with properties and buy into the sunk cost fallacy too.

Your best option would be to refinance your loan (if any) and get a construction loan for the improvements.

So it looks like you would need around 4-5 years to get to break even by selling those stocks and paying the tax now. 

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

Even still, it could be said that I've still lost money due to my time on the tools instead of prospecting as a real estate agent (the cost of lost opportunity).If you can truly do 80%-90% of the work yourself (at acceptable quality levels) and you aren't sacrificing your time where you can get better returns for your efforts, then yes, it can work even up here in Canada.

Get out and meet some other investors at meetups and that will help you curate what some of those ideas would be like in real life, with the input of others who have done it.

Since rent range is pulling from property managers the data is cleaner, because so many self managed property investors market their property way too expensive and they will never get that rent, it is just hopes and dreams.