New tenants won't be an issue, it'll be priced in and explained in their lease.But I do have one tenant in a 2BR who has a lease through January, and she'll need heat this winter.

Like is starting in the winter going to lead to a lot of down time?

I am estimating 30-60 days rehab time for the units which has them finished in the middle of winter, which isn’t the best time to try to get apartments rented.

He was defintely shady and drug this out almost two months which really cuts into my work time beforr winter which is going to out me out me way behind sxhedule but the money just makes sense i got him down 22k off his asking price and the avr I'll be in be in the mid 200krange.

It will pick back up in September before diving in the winter.

@Sochima Eze Especially consider no this variable is such an unknown... you may have a tenant that wears shorts all winter long and pumps yhe heat to 85!

Growing up in the midwest, I saw the wear winters cause to homes.Most of the things that you mentioned in the house that is "falling apart" are things that are usually at or near the end of their lifespan for a twenty-year-old house anywhere.If the house was your primary residence for at least two of the last five years you may qualify for a tax exclusion up to $250,000 single/$500,000 couple.

My family has recently purchased a home in Storrs, Connecticut, and I am looking for what to do with its enormous barn:                It is close to a big college campus and the winters hit hard. 

Finding tenants in the Fall is almost as hard as finding tenants in the Winter. 

@Marc Winter, thank you for advice, you are right of course about not being able to recover rent lost to vacancy.