I have had all 3 setups. I just made the switch from the 40' WW to a 40' DP.
If overall cost is a concern you will not come in cheaper then an older 5th. The new ones keep going up in price. The old ones seem to just stay at the same price year after year. Registration and insurance were less than $100 for the year. Very cheap. Tires are also cheap.
I bought an older DP. Mine is a 98 with 42k miles on it. 8 air bags and rides like a cloud. When I buy something I pay cash and tend to hang onto it for a while so the payment thing is not a factor. Registration for it in PHX was $400 until the year 2024 so $80 a year. I have buddies who have very nice expensive new DP's and some of them pay 1000-2000 a year in registration alone! Insurance is no more than adding another vehicle to the policy.
I was doing the 2 trailer shuffle going to the dunes and storing at GD storage. That got old after 2 seasons. I have plenty of room at my house to store and I missed having my rig here to tinker. We like to do tailgating, go to other places, nascar, Mexico, family trips etc. With 2 small kids its was a nightmare in the truck. Now like someone else mentioned above I have chilled the F@#K out. Set the cruise at 65-75 and crank the tunes. Kids, wife, friends, etc can simply enjoy the ride. IF we want to stop we can. I used to dread waking up the last morning in the 5th knowing all the picking up and take down work that was waiting for me before we could hit the road. Now its slides in, raise the jacks and let the coach air up while we say good bye to everyone.
I am getting ready to do a full remodel on the inside and once that is done I will have a very nice DP for a small fraction of what the new ones cost and I won't feel bad if I get it dirty.
I had the super C. Talk about a white knuckle drive. I would not wish that on anyone. A passing semi would damn near toss that thing off into the ditch.
Here is a picture of mine the wife has dubbed "The Blue Whale" in Deadwood SD. Did a 3k trip in it with the family in July. Was a blast.