If the furnace breaks during the winter and she needs to stay with family for a week that's a different story.

Nicer winters, easier on your roofs.

I want to have the 3 m2m tenants sign new leases with me because a) I'm going to use the BP leases which I feel more comfortable with, and b) I would prefer to have everyone in a 6 month lease so that I don't have to deal with people moving out in the winter and trying to find new tenants then... 

Therefore I wouldn't feel like I'm digging myself a whole starting out in fall/winter months when the market slows here, meaning less chances of sales yet still required to pay the monthly fees.

You're going into winter. 

With the lack of movement in our area, it's hard to say whether its worth securing the funds to carry the property through the Winter in the hopes of the market improving in our area and us finding a buyer.Josh - Feedback on the renovations we completed has been positive, with the main suggestions being that it should be under $2m, that the ceilings are low on the ground floor (8ft) and some of the guest bedrooms are a small for the price point. 

You are, in essence, trying to develop your own market assessment by utilizing shoe leather, door knocking, and some technology. 

@James Winters I think @Michael Lee did a great job of starting you in the right direction. 

Some make it sound like a full time job, I would say I don't spend more than 2-3 hours a week managing his property, even in the harsh winters of Boston.No LLC costs, etc.

If you can make them end during summer months it is easier to find tenants than in the dead of winter.