Steined, I'm not sure what is included in the service you mentioned either but if parking a boat in a driveway means putting it in a ramp I think a few minutes of practice at a local parking lot will probably help a lot. However, there are other benefits of on water storage that can't be denied.
One of my good friends had the same "dry rack" storage as Xoomer for his Rinker Cruiser. It was a lot more limited in that all they would do is take it down and remove the cover when he called in and they would recover it and restore it when we got back. He paid closer to $300 a month for this as I recall, this included outdoor storage for the trailer. For him it was worth it because he didn't want to buy a new vehicle to haul his boat around, didn't have a great place to store it at home and generally didn't like towing his boat around. It wouldn't work for me because I like to be near my boat incase I want to work on it. Also, I don't want to be stuck boating at one place. It always seems that I'm rusty at trailering, launching and recovering the boat when the season starts, if I put my boat in dry storage I would be forever rusty possibly to the point I would rarely if ever boat anywhere else. I also don't want to depend on someone else to do those things, with my luck as soon as I'm "hooked" the price would go up.
If you do go with a valet / dry rack service three things to consider based on my friends experience are:
1. Ask for a top rack if possible, anything else is subject to being hit by fluid leaks from the boats above it (sometime he boats on top get hit by bird shit, it depends on the facility chosen).
2. If you get back to the dock late what happens to your boat? In my friends situation the facility just had him leave it outside on the dock, unattended, until the next morning. My friend could live with that, I couldn't.
3. Find out if the service provider offer maintenance discounts or premiums for basic services like oil changes, tune up, winterization, etc. you should always be able to do it yourself but it is nice when you don't have to in that the boat is already at a "shop" but sometimes it's at a cost premium not a discount.