I don't know enough about your rentals to determine quality, location, or layout, but I suspect my numbers are pretty close.However, your utilities are pretty expensive in the winter.

Had excellent success self-managing as an Airbnb in the winter months and switching to a mid-term rental the summer months.

Although if you’re renting out right now in Boston winter will seem a little slower. 

Less people simply don't move in the winter.

The market has plenty of older properties that need renovation, a favorable refi environment, and is generally landlord friendly.That said, it's not all upside Cleveland has slower appreciation, harsh winters, and older homes that often require significant repairs.I sold over 50 value add deals last year and I can say that if you have even a "good" GC crew (doesn't have to superstars) you can raise and repeat this process all throughout the Westside and parts of East.

I'm sure you'll be out of here in the summer, but you'll love the winter. 

There's a lot DOM also but I expect during the winter. 

The rental market has slowed in recent months but expected in winter.

My only problem is that she refuses to turn on the heat even though its now winter and we are in the northeast.

Heating costs go up in winter, as does electricity due to the reduced natural light and more people indoors.