you say ... unfortunate. New rules came in a few years back that I don't understand yet, but bottom line is that to trailer a boat as heavy as a 26 footer likely needs the load and tow vehicle inspected annually. As in a matched pair, so you can't just own a boat and trailer and have a buddy with an F150 haul it for you twice a year. So a 26 foot boat on a trailer in Ontario may not be legally practical. So the trailer practically speaking may only be useful at the yacht club grounds, not on the road.
Now if you hire a boat moving service
that takes your trailer and boat as a load on their already legal
rig, then that is a different matter. I had my 32 foot 10,000 pound boat and cradle
moved about 250 km for about $1200 (or was it $1400, I forget.)
It is not clear to me if the professional boat trailers can load a smaller trailer or just a cradle. If I had to guess, I would think this is possible.
I used an outfit in Midland, ON. PM me if you want the contact info.