As it has been said, I would tend to lean towards continuing to rent.

Continue to reach out online to others that can give insight on these areas.

If your short term rental is advertised on a platform not doing this, then the operator must continue to report and pay HOT directly to the city every month.

could do really great charitable things with that kind of money) and more than likely even if retired at a young age, I plan to continue investing and scaling. 

Then you take those funds and roll them into the next deal all the while continuing to grow your investment.

You have about $280,000 in equity in your home and you want to put it to work doing a fix and flip this year and continue that model.

The lessons I’ve learned will undoubtedly guide my future investments - this journey is continuing! 

The part that seems to continuously get people (unfortunately, and for lack of better words) is the "no evictions, no bankruptcy, and no more than 6 non-medical collections." 

I enjoy a healthy debate and learned a lot from this thread 7 months ago and continue to learn from it today!

We both were approved for a 180-month 5.85% loan, as well as a 7% 30-year fixed mortgage, but we will continue to shop around with the idea that we would just pay off the entire mortgage once our funds become liquid.