Be aware that most boats that need TLC will require more money to restore them than the difference it would cost to buy the exact same boat in decent shape would have cost.
I would highly recommend you look at James Baldwin's Boat List
, as many of the boats on that list are reasonably inexpensive and capable of doing what you're looking to do.
I'd also recommend you read the Boat Inspection Trip Tips
thread I started, as it will help you determine whether the boats you look at are even worth going forward on, saving you the price of a survey on boats that aren't worth looking at further.
A few other questions:
1) Do you have a place to work on the boat and store it while working on it? If not, then you'll be paying yard storage charges, and that can get expensive quickly.
2) Do you have the tools and skills to do a restoration? Restoring a boat will require most of what I've listed in my Boat Tool Kit post
3) Do you know how to sail?? A lot of people start this type of project, only to find out that they get brutally seasick... If you don't have any experience sailing, get some first.
4) Where are you located?? My guess is in the Maritime provinces PEI, NB, NS, since you're talking about Eastern Canada and the Northeastern US. Buying a boat that is geographically close to you will reduce the costs of transporting it.