All depends on the truck. If it’s you DD you’re giving up usability the bigger you go. A 1/2 ton that would make a nice DD could comfortably go to the 8-10k range on a good trailer.

A SRW Diesel will give up some ride comfort to a 1/2 ton but is still as useable and parkable otherwise. Maybe 10-13k towing.

Beyond that you’re talking duallys and then medium duty’s. If you can afford it and have space for extra vehicles, great. For me, I’m in the market for an extended cab diesel.

As far as towing, my ~40’ trailer is challenging. I’d towed “normal” boats up to 23’ for years and was quite comfortable with those. There weren’t many places I couldn’t get in and out of.

The 40’ trailer requires more forethought. You can pretty much treat it like a big rig. So that limits where you’ll be stopping and fueling up and eating etc.

Also: ramps. You’ve got to ask ahead about which ones to use. The break over angle mine can handle is very shallow.

I have a nice triple axle with about 9-10k on it. Tows great, you’ve just got to think and plan ahead more than just hooking up your 20’ boat to the SUV and heading to any lake with a ramp. Good luck.

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Most 40’ or smaller you can pull with a Srw 3500 on a good trailer without many issues.

I’ve towed our 43 Donzi all over, but that’s more long than big.

This past summer my wife and I took delivery of a new Monterey 335 Sport Yacht. We enjoy traveling to different lakes and areas, and wanted the largest cruiser for this purpose. I wanted to keep the beam under 11’ so the 10’10” was perfect. I’d easily go up to 11’3” or so now.

I had Myco custom build a 10’ wide trailer in order to get the boat as low as possible. I take the radar and pedestal off, and am at 13’6” exactly. I made it so it goes on/ comes off in about 1-2 minutes.

This summer we towed it 4,200 miles to various places and had a blast. Definitely very happy with the setup and it’s pretty stress free. I have a truck GPS that I have 14’ height programmed in so it routes me where I can go. Tow it with a 2018 Ford F450 which is also my DD. https://cimg8.ibsrv.net/gimg/www.off...201c6e231.jpeg
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Bingo!

I am always shocked at some of the trailers I see.

From people w/no straps (I don’t need em??), to no trailer brakes, no spare etc.
When I pulled my lil 25’ home from Philli the seller thought I was a sissy for wanting a spare tire and straps for the boat!

My favorite though is the high dollar boats on a trailer w/bunks that stop 3’ short of the transom and the bunks hanging off the end of the trailer frame by 3+’.
Yikes.

Wow!
Well Done sir. Your forethought and engineering is repaying you well.
Excellent.

Great point about break over point.

I once watched a 30’ Searay drag a 2 whd 1/2 ton down a ramp, driven by an elderly guy, w/his adult son on the bow of the boat (!!), as it headed for an alum fishing boat tied at dock, full of people while the red neck owner walked beside the skidding truck, screaming through the window at the driver!
I pointed out to said red neck, that he might want to get the crew out of his boat!
I then stood guard over the driver until the police showed up.
What a disaster!