I trailer my boat and I launch it at the ramp. I towed it with a Chevy 3500 HD Dually (06), Freightliner Sportchassis, Chevy 2500 HD, and Dodge 3500 dually (2011). We launch my boat at the marina with an 06 F250 6.0L. The launch ramp is right next to the marina.
When I was towing regularly, I bought the Freightliner and it towed it great. Felt very comfortable with the set up. With the 06 Chev Dually, I did not feel comfortable on the highway, therefore I got the FL. In town, taking it 5-10 miles, I used the 2500 HD and that did just fine. You take your time and drive the speed limit on the road, the truck will do the job just fine. We launch with a 3/4 ton truck and it does it without issue.
For longer distance, either a medium duty or the Dodge 3500 dually is the ticket. My Sportchassis was awesome, but it cost $100k. I towed the boat to San Diego from Phoenix (400 miles) last July with the Dodge. It did excellent. If I was buying a truck today to tow my boat, I'd buy the Dodge. It's $50k less than the FL and it fits in a garage.
My boat is 45' long on the trailer (extended swim platform) and 14' 2" tall.
Weight of boat on trailer is 22-23k.