Russ, Welcome aboard!
I believe that the transoms are foam--My 2006 boat has a foam transom. Any cored hull of any sort, should have the holes drilled slightly oversized, then core material routed out for about 1/4 to 5/16" around the hole, with thickened epoxy. This prevents any core water intrusion, and crushing of the laminate as core is compressed.
The factory shipping direct does undercut the dealer network--but they certainly have done this in the past--and any really good marine shop can rig a boat, and handled warrantee work. In the past I have done my own--so I knew it was done correctly, and took less time than trailering the boat many miles to a dealer.
There are several 22's and 23's in your area--I suspect that one will offer you a ride. I don't know how up to date the C Dory Map is--but that is one source--and ask for a ride. Most owners are always happy to give one.
Of course a C Dory can tow a 200 lb water skier. I have water skied a number of times behind a 25 hp outboard. The Chris Craft I learned to ski behind had only 60 hp. I have towed my grandkids in tubes--others have towed skiers.
Do remember that the boats are "semi Dorys" That means that there is little deadrise--they do take getting used to, for going into chop--on the other hand, one likes to have smooth water for Skiing.
My current 22 came with a 5200 lb rated trailer single axle. The tongue broke going down the road--I was near the load limit. Most C Dory's are gong to come in closer to the 4500+ point on the trailer. We now have a tandem axle trailer rated for over 6500 lbs--no more difficult to maneuver--we park it in a space 10 feet wide, after backing in about 150 feet, with a gate only 10 feet wide, about 25 feet in front of where I park my two boat trailers. My other boat is on a single axle trailer, and they are about the same to maneuver. Single will be fine, if you are not towing across the US--as we often do.
Trailers have to be less than 8' 6" wide. Ours is 27 feet on the trailer. Generally the C Dory trailer is at least 8 feet wide.
6 hp should be fine for a kicker. I have used both the Torqeedo Traveler 1003 and a 3.5 hp Merc 2 stoke (my dinghy motors) as kickers. The hulls are fairly easily driven in calm water. Bucking into head seas, it will be faster with a high thrust 8 hp or 9.9 hp.
I don't know how much the brand new C Dory 22 is currently, but I suspect it would be fairly easy to spend over $75,000 for a decently equiped boat. There are many options. There is a new boat for sale in Seattle for $68,000. There is a loaded 2014 boat for $79,000 in Wi. There will be at least $3500 for transport fee. For items such as the Windlass, refrigerator, 110 V electrical, trim tabs (essential) , swim step and ladder, it would probably be best to have it put in at the factory. Electronics can be as simple as a 5" combo chart plotter with fish finder for $600 plus installation if you don't feel comfortable. (should not drill holes in the transom without potting. You can easily spend $5,000 for a radar, auto pilot chart plotter, downscan/side scan solar, plus fish finder with CHIRP. VHF radio, best with AIS receiver--or even the Class B transceiver, if you boat where there is heavy commercial traffic. Don't forget the compass.
Basics such as life jackets, anchor, flares, are gong to run in the $500 to $1000. If going offshore a
The factory should be able to give you precise numbers for each option which is listed on the specifications of the 22. I personally feel that a local canvas working is best for the Camper back with Bimini.
The ski tow eyes, may be an option these days, and they should be potted with epoxy--as I noted above.
I always figure 25% at least over the purchase price of a boat for "options".
Have fun, ordering and outfitting.
