Those are very different boats, each designed for a particular use. From here, this is one guy's opinion...
That era Tollycrafts are nice boats, heavily built. If your usage is staying on the water and essentially cruising one area, a well-kept/maintained Tolly would be a good "cabin on the water" or slower cruising boat.
Your Cape Cruiser is a trailerable boat that gives up beam and length to be reasonably easily trailerable. While your usage may currently be all that you can reach from the Birch Bay area, if you decide to trailer other places, the opportunities are unlimited. Florida Keys in the winter, the New York Canal System in the summer... you are only limited by time and money.
There is something to be said for beam and elbow room, and the Tolly has that in spades over the CC. If the Tolly you are considering has a fly bridge, that is another interesting consideration. Bigger boat > bigger maintenance > bigger marina costs > more expensive to haul out > bigger fuel costs. Inboard vs outboard makes a difference in ease of maintenance and being able to haul the boat to an inland facility vs using a boat yard with a travel lift.
If I were truly living onboard (we spent up to 6 months at a time on our CD-25), I would certainly be looking towards the bigger boat. If I was looking to take a boat to all the interesting cruising places on a trailer behind a truck, I'd be staying with the CC. An older boat can be a huge money pit if it is need of updating; are you able to do the work yourself?
This isn't apples and oranges - more like apples and watermelons; the apple you can put in your lunch bag and enjoy on the go; the watermelon is going to take up more space and be more work (slicing, plates, refrigerate after cracking it open) to enjoy.
Good luck with the decisions.