Hi Ben,
I'm an investor-focused agent in Windsor. Sounds like you have three good properties with plenty of equity, so it's a difficult decision. Do you live in one of these properties?
Top of my head withought knowing all of the details, the condo seems lease likely to cash flow and will likely see lower percentage returns than your other properties. This changes, of course, if you're living there as a personal residence.
If your tenant in Windsor isn't paying, then that certainly brings it into consideration for selling. Fundamentally, holding single family homes in Windsor is a good long-term play because we have a significant shortage.
The last point I would make revolves around your long-term strategy and what you plan to do with your capital long-term (other than using it to close condo).
