Rents have softened especially since covid.

It is much harder to cashflow here, though not impossible.Either way, it sounds like the best course of action is to sell, 1031 and redeploy your capital.I do anticipate the market to soften a bit as more homeowners decide to sell as the vaccine rollout continues.

On the inspection, there were electrical issues, garage roof is close to needing replacement, 5 years on the house roof, appliances are old, including one furnace and water heater, no water softener, windows are old, old chimney, garage doors need repair, baths/kitchens are outdated, but still functional, could use better sloping for the drive/yard, and this list isn't all inclusive. 

On the inspection, there were electrical issues, garage roof is close to needing replacement, 5 years on the house roof, appliances are old, including one furnace and water heater, no water softener, windows are old, old chimney, garage doors need repair, baths/kitchens are outdated, but still functional, could use better sloping for the drive/yard, and this list isn't all inclusive.

Others will just soften. 

The one thing I will say that is finicky is the electric on-demand hot water heater: it doesn't like it the hard water from our well so we had to upgrade our water softener to the best one available, and it also doesn't like it when my wife runs the dishwasher, clothes washer, and tries to take two long hot showers at the same time.

I'm very conservative about buy and hold because I am not at all convinced that between all the money being printed and the years of appreciation in Massachusetts, the current real estate bubble and migration patterns, the market won't soften or even tank here.

If your long term strategy is buy and hold just make sure you are being conservative with your repair, vacancy, property management and capex estimates (which you are) and you will be fine if there is a softening in the rental market. 

Calgary has seen a softening of their rental market with increased vacancy rates, especially in the downtown core.

We keep hearing that in 2021 real state investments will likely see a softening of the market.