To get back to the OP's questions. I was in the same boat (looking for my 'forever' trailer). 2500, tractor, existing 16' 10k# trailer. Trailer was barely adequate, if I only had a light implement and kept the speed down.
Decided I hated moving ramps around, tested a parked new heavy duty PJ flip ramp -- too hard (not well balanced torsion spring). Decided on a 22' deck over hydraulic tilt. No ramps to worry about -- ever (my concerns are more that something happens when you are out with the unit, like slipping, dropping something on your foot, any stupid moment kind of thing). Plus, I haven't figured out how to get younger.
Though I wasn't looking for a goose neck (I know, not on your list) I ended up with a PJ T8 gooseneck. Never again will I get a gooseneck in this size range (out of scope for your particular question).
14k# means I have enough overage for the tractor and an implement or two. No CDL concerns, as it's very unlikely I will own a dually. 22' tilt bed, plus 4' fixed section, winch. Deck over is the only way to go. I've only used mine with the tractor on it a couple of times. A little sphincter activity, but nothing especially challenging. Load other vehicles, large bales of hay, long 'stuff'. And be able to unload them at home. Forks will be a god send of owning a tractor. You use them so much more than you thought.
With the old 10k trailer, I had various cars and a skid steer that required a lot of work to get ramp angles correct. And I don't want to loose flat bed length to a dovetail. With the deck over tilt, all is well, and no issues with pushing vehicles (and there is never enough people around to make that truly safe, etc). Just untie everything, hold the controls (winch in one hand, tilt in the other; for affect of course). Moved a couple of car bodies that had at best questionable rubber devices formerly known as tires, etc. Bed height isn't much different than the bed of a 4x4 2500. Doesn't matter much from the cab with the forks on anyhow.
Though it hasn't mattered to me (yet) the fixed section means I can put something there (implement, skid steer, etc) and then tilt the trailer back down to load the rest.