If the home needs that much work and you don't have the money, sell it. You may consider holding it for a while to see if the market changes, which could happen in the next 6 - 9 months. Spring is probably the best time to sell and get the most money on this investment. Also, consider borrowing the money from your own home (if you can) to make the repairs. Only make the repairs if your return on investment is substantially more than $100,000. Be sure to get several opinions on the current value and what the value may be worth one year from now.
do a re-hab. I wouldn't wait out the winter - price it right and sell it. Interest rates are still good. For you, it is all about pricing. Speak to your realtor.
A trusted Real Estate agent would be your first step. Ask Him/Her about your homes' current market value, and it's potential maximum value. Next, list your specific proposed changes and expected return and ask local contractors for quotes on construction costs.
Many home builders and subcontractors are looking for work now, with the new construction market slowdown, and financing your renovation work with the homes equity, or even finding a contractor willing to accept partial payment after the sale is a very real option if the right incentive is provided. This "bad market" is providing many options that were previously unavailable.
And frankly, anyone that can give you next years value on your home, after expenses, would be dealing with a crystal ball which doesn't come with a Real Estate license.
The truth is, the market has only adjusted in most areas of Massachusetts by about 8% over the last several years. If you use a 5% margin of era in calculating your improved value looking towards a springtime sale, you should be able to get the answer your looking for, a significant profit, if it's there to be had, and not be left second guessing your decision.
I would sell as is and price it accordingly. As far a when to sell. That would be up to you! If you have the property priced right in its present condition, I would be sure to market to investors or folks that would want to buy, fix up and resale. Good luck!