George,
Two things:
1) The guy who purchased my chipper said he went around and looked at a few of DR chippers used, all with 18/19 HP motors. He said most of all of them were in the $1,500 range. However, they looked used. He said he was buying mine because of the little use it had. If I were you, I wouldn't go any higher than $1,800 to $2,000 with all the extras. (Electric start, two package, extended discharge chute)
2) The chipper was nice to use to clean up with. (Sure is easier than towing the Vermeer around the yard) Nice and light I could just walk by hand anywhere I wanted to go. The real deceiving part is the size of log it can handle. Most chippers limit the size based upon power. I.E. If you look at one of the little chippers from the Big Boxes, they will claim a 2.5" or so maximum size. If you put and actual 2.5" into it, it will practically stall out. However, with the DR chipper, You could jam a 4-4.5" limb in there and it would not even hiccup. The problem is, the opening was only 4.5", so the limb had to be perfectly straight and all the branches had to be trimmed. So in reality, most limbs were in the 3-4" range and heavy limbs still had to be trimmed.
If you are doing light yard cleanup, I would get one used. Especially if you have a gator or something to pull it with. However, I would not pay anywhere near the full new price, I would personally rather get a commercial chipper used at auction.
Hope this helps, if you want to know anything else about it, just ask.