This is going to be a personal preference, but for me, the short answer is yes! Our first fifth wheel had an automatic leveling system and I really got spoiled with the convenience and the amount of control. Our current fifth wheel doesn’t have it, and I find the lack of control frustrating.
With the auto level system, I could control any of the four landing gear individually from a central control unit. With our current fifth wheel, the fronts go up and down and the backs go up and down. There’s no individual control. If you’ve never had that, you don’t know what you’re missing.
The cost of the system when added later is around 4k, but when it’s included in the price of the trailer, it’s not a large percentage in my opinion.
Bottom line for me, if/when we buy a new trailer, it WILL have an auto level system!