Dad has a Vermeer 8 wheel caddy-type rake like the one your son just bought. Works good except in real heavy hay, will bunch up under the support arms and make a huge knot in the back. You can take the pins with the clevis-type retainer clips out and put bolts in upside down with locknuts on top if it turns out to be a problem for you. For the money, they're a great rake, I'd suggest tying the back wheels together when you raise them and go down the road. I smacked a yuppy car with his one time on a narrow bridge.
I've got a 10 wheel frame type Vermeer that folds horizontally instead of vertical. Biggest plus is you can adjust raking width as you drive and I've yet to plug it. It also hugs the ground a little better and folds down to 8' wide for towing. Biggest complaint is it binds up in the folded position and is hard to start spreading out without a few jerks from the tractor.
Both good rakes, but the latter is more versatile.