After pulling 23-35 foot tow trailers for years I lost one. I had a brand new 99 Dodge Shortbed with V10 which pulled everything (it also passed everything but a gas station) but it had a faulty hitch. I lost the 23' trailer after it came off the hitch with antisway bracing etc and flipped 3 times in the air before crashlanding. I made the 2 minutes of fame on the news. I was coming down a very steep hill and speeding up and slowing down and using the trailer brakes did not help. The whole thing lasted about 3 miles. Luckily all the other freeway drivers stayed back and no one was hurt. Dodge recalled the hitch stating that it could cause the trailer to come undone and cause an accident. I became a recall statistic.
But that's not the story. I switched to a fifth wheel on that shortbed and have since upgraded to a 1 ton longbed and I would never go back to Tow Trailers as the fifth wheel seems to become part of the truck when being pulled. It's a whole different world. (Of course as all of this, is in my opinion (IMO they call it here).) My current 5th wheel is a 28.5 which is really 30 overall length and it tows like a dream. I dry camp allot and go up mountains that are very steep in mud, rain, snow and etc and have for years with both types of Trailers. I like the 5er best.
Yes, it was quite an experience. The metal fatiqued and was warped like an S on both sides of the hitch bracing. There wasn't anything else I could have done.
But, about your question, there are other things to consider such as ease of hooking up and unhooking. If you get power trailer lifts on your TT and leave the main hitch installed all the time they are almost equal in hooking up. I can hook my 5er up all alone. I also could hook up the 35 by myself with the power lift. (Just had to jocky the hitch to the right spot by getting in and out a couple of times. The 5er I just sit up a little and look back and drive it right into place. It auto locks as I put the pin into place. I call the 5th wheel hitches Saddle Hitches (I don't know if that is proper but it makes sense to me). I can remove mine (which I only do occasionally) and all that is left are the two mounting rails in the bottom of the bed. I also have a 5th wheel box at the front to haul the king pin stabilizers etc.
I did knock out my rear window in my shortbed once even tho I have the extended hitch on the trailer. So make sure you get the sliding hitch that eveyone here talks about if you go 5er. (Regardless of whether you get the extended hitch on the trailer.)
Overall the ease of loading and unloading the 5er is still a bit better even with the TT having the power hitch. You also really extend a shorter distance behind the truck with a 5th wheel as a certain amount is located over the bed (of the overall length) which may be part of the reason it feels so much better towing. That combined with the hitch over the rear axles instead of at the bumber better distributes the weight. The only 5ers I've seen that tilt the truck are usually because they did not get the proper height adjustments when matching the two up. I see tons of people driving TT with the front of the truck up in the air from over loading, incorrect weight distributions and/or truck limitations (even with the antisway bracing and levelers). I suppose that it boils down to making sure you match the 2 in either case and pick the floorplan that best fits your needs. I will stick with my 5er tho. (Maybe I have just been spoiled!)
Be aware tho that you lose access to the truck bed (other than limited storage) when you pick the 5th wheel. You can use the whole truck bed with a TT. Sometimes that is a deciding factor. (Like where do you put the paddle boat???? (right))
Voyager20 gave you some good info. I have towed both and the fifth wheel is by far the better for towing (IMO). Do get the slider hitch and match the trailer to your tow vehicle. Watch the weight
Pull-Rite has a hitch for 'bumper pull' (TT) trailers which they claim makes it tow like a fifth wheel (5W), and makes it easier to hook up to boot. The advantages of the 5W are usually a taller interior height, often more storage, a shorter overall rig length and it tows well/hooks up easily with the simplest of hitches. The disadvantages, you must have a pickup, you lose much of your truck bed, it adds a lot of weight (often too much) to the rear axel of the truck, short bed pickups require sliders and/or extended pin boxes, wind resistance/low clearances can be more of a factor and there is a set of steep steps inside.
I have to agree with everyone else, 5th wheels are the best! Expect to pay more for the rig and hitch though. I'd say around 20% more for each. but when your on the highway and a semi passes you the extra money will be completely forgotten about. When we had a TT and I saw a semi coming to pass me, I would tell my wife, "get ready for the push-suck"! As the semi was even with the TT it would push the trailer out, then as it passed my truck it would suck us in. Even with anti-sway and weight dist. hitch! Now that we have the 5th wheel I say to my wife a a semi passes us, "remember the push-suck?" Her reply is usually, "unfortunatly, yes".
I guess you can't fully apreciate the 5th wheel unless you have owned a TT!