I have the original Hensley that I bought in 2002, I'm in Islip if you want to come over and look at it. Just rebuilt it last year with new bearings and seals.
The Hensley and the ProPride both use the 4-bar principle to control sway and are equally effective, they are the only two hitches using that design. The ProPride was created by a former Hensley employee who broke off to do his own thing and create a "new and improved" version of the Hensley Arrow. Personally I don't see any advantages, I would buy whichever you can get on sale.
Whether you "need" a premium hitch depends on a lot of variables, including the wheelbase of the truck and the design of the trailer. Personally I wouldn't tow without my Hensley. I recall you saying on the tow vehicle forum that you are getting a toy hauler....those are built VERY nose heavy to ensure adequate tongue weight when you load stuff in the garage behind the axles. One member here (carringb) busted up a Hensley running over the 1400 max tongue weight rating, so you may want to hold off buying the hitch until you settle on a trailer.
As far as hitching up, I'm out in the beach with it and no issues hitching up on the sand at all kinds of odd angles. Takes some getting used to, but not overly difficult.
