I would caution you that even a 22' trailer may be too short, depending on what attachments you want to have hooked up to the tractor. Case in point, my 18' trailer is about 3' too short for my tractor with FEL when I have the brush hog on the 3 pt.
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Now, if I wanted to also have another attachment along for the ride, like a rake or a tiller strapped down in front of the tractor, I'm looking at 26' to 28' of deck space. I'm looking at 28' goose deckovers myself for this reason.
It may not be absolutely necessary to have a trailer with a deck long enough to accommodate everything you might bring along.
I bought a 14K - 20' equipment trailer, when I would have preferred a 22' or 24'.
Why?
Because It thought it would work for me, and it would leave 14' additional for me to store my Jeep ahead of it for the winter.
I have adequate storage square footage, but never enough organization.
I knew that my backhoe bucket would hang over the trailer rear by 20", and that my loader bucket would need to be curled over the trailer front.
It was a bit of a guess for weight distribution, but it has worked out great.
TLB + trailer = exactly 12,000 lbs. Tongue weight 1250 Lbs. Perfect!
I put a red flag on the hoe for towing, but it is less than 2' beyond the tail, so not legally required.
Of course if you store your trailer outside, the length would not matter.
I store no tractors, implements, vehicles, or trailers outside.