Re: What is the maximum size for a boat if you really want to trailer it?
What size boat would be the max/largest you could get if you really want to trailer it and not keep it in a slip?
Let's assume by "trailering" you mean keep it on the trailer except while being used, and also driving to and from the ramp some distance (v. dry slip). And you are considering something 21' or bigger.
In addition to the tow vehicle you should take a good hard look at the ramp(s) you will use. Piers along side, crowds, and helpers if you are solo or otherwise without capable help to muscle a big boat around in challenging conditions. Road conditions and traffic along the way. And where are you going to store that pig when you get home?
And look at your physical abilities and tolerance for challenges (and that of your crew). Do you really want to start your day, and worse, end it, wrassling a big boat onto a trailer in the Mississippi heat? Every day? (maybe a short-term wet slip is available).
Being on the coast, you don't need to trailer from lake to lake or get tired of being stuck on the same one. This is one of the many reasons why the trailer life style works for fresh water lake boaters but not salties.
i know I regularly beat the "roller trailer" drum for salt water boating but a big one will most likely be dunked. dunk it every time you go boating and it will take a big toll on your trailer (does your ramp have hoses on the ramp and can you hose off there? I can b/c it's a club; can't do that at a busy public ramp even if it had hoses). There is no such thing as rust-proof and water tight. and that trailer being a dual axle with brakes has lots of expensive parts to go bad. You'd be trading cost and convenience to slip it against savings, hard work and buying new trailer parts constantly.
I don't think twice about trailering and splashing my 17' and 19'. They are single axle and have power winches. I don't enjoy it with my 21' on a dual axle and would not use the boat much if that were part of every trip, but lots of people manage that rig just fine.
I really think that just because you can do something, and that other people do it, that you should do it. There is a point where trailering some boats is possible but not practical. Trailering big boats regularly is a relatively new thing, fitting in the "super size me" culture for everything we do. But since the point is to enjoy boating, and you have to spend money to do it, pay to slip it or buy a smaller, more managable boat.