If you're considering overnight, then berth space is good. Only problem with traveling in enclosed cabins, is people who are prone are much more likely to be seasick. A canopy (retractable canvas?) where you can get a bit of breeze but still get out of the sun or rain is nice. Or you could have a hardtop strong enough for those who want some sun to lounge up top.
I don't get to Toronto very often. I do usually go down to The Outdoor Adventure Show
The Outdoor Adventure Show - National Event Management which is Feb 22, 23 &24 this year. Don't know for sure I'm going or what day yet. But we could hook up there if you'd like.
Every boat is a compromise. You need to decide what you want it to do and then look for the best fit. For example, for speed, weight is a major factor. You need to get the boat planing on top of the water, the more weight, the more power that requires and that means major fuel bills. For a displacement hull, max speed is a factor of your waterline length. Theoretical max speed in knots is 1.4 times the square root of the length of the waterline. So if you've got a 25 foot boat with a 22 foot waterline, you max would be 6.57 knots (7.56 mph). Move up to a 35 foot boat with a 32 foot waterline and it's 7.92 knots (9.12 mph). There are still weight vs power factors, beam (actually a wide beam can increase the actual length of the waterline) that will affect your actual speed. That part of the reason for supertankers and large container ships. The same power plant will move the longer tanker faster and still require the same size crew. Limiting factors become port capabilities and enough strength that the ship does break in the middle. They actually have to be careful loading/unloading now days, as too much in or out of a tank and the ends or the center, could break a ship in half!!!!
Anyway, keep in touch, maybe PM me a week or so before the Outdoor Show and we can set something up. You could consider a Canadian Power Squadron Boating Course (not the Boat Pro) to pass the winter. Even if you're hiring a captain, being able to operate and navigate your boat would be an excellent backup.