I kept my 17’ HPX-V on a drive on dock, mine is made by VersaDock, for 9 years and now I have my Evo x on the same dock, though I had to pull the dock’s back end apart and reconfigure it for the very different shape and weight of the new skiff.
So far, the drive on dock is less maintenance and worry then my lift, definitely not cheaper to get into, but probably going to be cheaper in the long run. That said, it’s not maintenance free, I’ve replaced the sea wall brackets and have to occasionally tighten the pins and maybe once a year I scrape the grass off the sides.
As for the skiffs, the process of driving them up on plastic will find the tiny weak spots between the gel coat and the rest of the hull, I had at least a dozen on the HPX and it was pretty much a ‘one and done’ kinda thing, not a recurring problem. Most of these were a few millimeters in size, none bigger then a cm. The Evo has only lost a bit of gel on the poling strakes.
As for on and off, the HPX was so heavy in the aft end about a square foot of the Hull was constantly in the water, so I was always cleaning barnacles off that little bit of hull, really not a big deal and when I sold it the new owner never noticed. The Evo stays completely out of the water, but I have to push it the first few feet to get her off, again not a big deal for me. I was able to back the HPX off with power. I keep spray silicone handy and a couple times per year use it to lube the dock, make on/off easier.
Your picture looks like the skiff will lay on the runners and not directly on the plastic blocks, my first impression is that’s better, more like the trailer bunks, as long as the plastic bunks are in the right place. My experience is with the modular dock, so I’m not sure about that design.
When I was shopping skiffs Hells Bay said no problem with using the drive on dock. Curiously, changing trailer brands voids your warranty, but they said the drive on dock was okay.