I want to be clear that I don’t think 5ers are a bad thing. They do provide a lot of storage and such, but when it comes to pulling I do prefer a TT.
1. Hooking up is easier. Once the pin is in the saddle, it is harder to connect the umbilical and break away cable on the fifth. Everything is easier to reach on the TT. There are fewer steps to hook up a 5er, but a power tongue jack is almost a standard these days which makes setting the bars pretty easy.
2. Turning is easier with a TT. With a long 5er turning right at an intersection requires pulling into the intersection before starting the turn. It’s the same problem semi’s face. Traffic can be a real pain. The TT tracks more closely behind the truck and kick out is reduced.
3. Wind- the fiver is generally taller than the TT. They are the same width though, which means a fifth wheel is going to be more top heavy than a travel trailer. Also, the WDH on a TT does provide some additional down force to the TT axle(s). I feel the TT is a bit less likely to blow over than the 5er, but if it does, it’s likely to cause less damage to the TV. I had a TT blow over, it popped off the ball. I had to cut one of the safety chains to get free, but when I did I was able to drive to shelter. Another driver pulling a 5er wasn’t so lucky. It blew over, destroyed his truck and put him in the hospital.
4. I’ve seen a 5er hit an overpass, never saw a TT tall enough to hit any overpass.
A TT is more susceptible to sway than a 5er, but it can still happen and there’s nothing you can do about it but slow down. Last week I pulled a 5er 900 miles that jerked the back of my truck side to side any time I hit 65 mph. Brand new camper, completely empty. It might tow fine loaded to camp. I sure hope so!
5ers and TTS back completely differently. I tow campers ranging from 17 feet to 44 feet. I can’t back a 5er worth a hill of beans, but I can put any size TT anywhere you want it. TT’s are much easier to back up.
Finally, pulling a TT leaves the truck bed free for carrying stuff.

Those are are pretty much the reasons why I prefer a TT to a 5er. There are exceptions to everything, though. With the bedroom hanging over the bed of the truck a 5er rig is going to be shorter overall than an equivalent TT floor plan. Lots of different priorities drive the choices people make.

Congrats and safe travels.

Nice upgrade! Looks great.!