I am bumping into more and more people that I consider fairly high achievers that seem to have someone coaching them to do better as well.

Talk about aiming high, right?

Some theming is basic and some is overdone, try to be unique or at least high quality, not a place you want to skimp.

Besides that, just wanted to chime in real quick - I'd highly check in with a CPA and I am no tax expert, so wanted to preference that.

However while people in Windsor doesn't have the luxury of high paying jobs that GTA residents have, is it just a temporary fever of buying houses, or there is really something going on in this city ? 

The house includes high-end upgrades such as custom cabinetry, granite countertops and energy efficient appliances.

Key Questions:Would it be more financially prudent to sell the rental property and pay off a chunk of my high-interest primary mortgage (7.375%), and use the remainder for a fix and flip?

Medford (North Boston) happens to be a low supply/high demand market so I absolutely need to get more comfortable with consistent rent increases but those increases need to be researched and in line with the market. 

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

Being a real estate professional allows you to treat the income as non-passive, allowing higher high income tax payers to pay less in taxes.