I went from 2 TT's to a 5er and back to a TT.
Biggest pros and cons.
Pros for the TT
One floor level
Lower ceilings
Usually less expensive
Cons for a TT
Dealing with a WDH
Not being able to walk between the truck and trailer when hitched.
Prone to sway
I never worried about the 5th hitch as it stayed in the truck the whole season except for needing the bed maybe 1-2 times. I have a 5'x10' utility trailer to haul things if needed.
I like having 2 curb side doors as well. Lower overall height makes cleaning and waxing easier and not having to worry about low fuel station roofs.
Hitching the 5er is IMO way easier. Also no dealing with spring bars and a heavy WDH every trip.