We started out without a trailer. We had a boat dock on the back of our house in saltwater in Charlotte Harbor. Take four lines off and away we went. This worked great for nearly 4 years. We had two elliptical pontoons, easy as pie to get underneath and clean them.
Fast forward. We move back to Ft. Myers, and get a wet slip at a nearby marina ($180 per month). We replaced the dual ellipticals with the tritoon SPS. A nightmare to get underneath it to clean. Having to work on the inboard sides of the outer pontoons, as well as cleaning the center pontoon is extremely difficult. I've taken my scuba gear, anchored in about 6' of water and got underneath it to clean. More of an effort than I prefer to do. I anchor in 3-4' of water, on my knees, frog-walking between the pontoons. Still difficult. Compounding all of this with the simple fact that I've now got a 3rd pontoon to clean.
I finally decide that I'm going to trailer the boat. The problem is, I now need a tow vehicle to do this. The good news is, I was in the market for a new truck anyways, so I just made sure that my new truck would be capable of towing 6,000 lbs of boat & trailer. 2016 Nissan Titan XD SL diesel.
I had a custom trailer built by Owens & Sons in St. Petersburg, FL. Beautiful trailer, exceptionally well built (aluminum frame, SS brakes, LED lights). The cost was about $1,000 or so above the regular stock trailers, but it truly fits the boat perfectly.
We now take the boat to many more places than we used to go in the past. We were very active with the boat, and would think nothing of going from Ft. Myers as far north as Sarasota, and as far south as the Keys. Still, having the boat on the trailer now makes it exceptionally easy to go.
I've also noticed that I take much better care of the boat. I bring the boat from the storage location over to the house, and can get a lot of work done by myself that in the past I had to rely on the dealer to do.
So all in all, I'm personally much happier with the trailer. Wish I'd have done it years ago.