Art,
I have done a bit of experimentation with various small antennas, in comparison to larger full sized antennas on boats. For the C Dory I prefer the "Ham Sticks" They work with a rail mount on the cabin top hand rail. Then you can ground the rail with 2 to 3" wide copper strap, running across the inside of the cabin, and aft to the engine. Not ideal, but probably the best you can do with the small cabin.
As well as Ham Stick, there is Hustler, Pro AM (not sure if Larson or Comet still make HF base loaded types), and I just read that Ham Stick is out of business-but some antennas are still available. I had some issues with the pot metal used in the ends of the loading coils on the Hustlers, after extensive maritime use. But I have worked all of the S. Pacific and Asia, some of Europe with Hustlers mounted on my RV. Also worked from Europe to mid US with Hustlers mounted on the stern of the large sailboat we took to Europe.
However, there is a better way to get around the ground problem--and that is to make a dipole out of the ham stick or other base loaded antenna, such as the Hustler. Here is an article about doing this:
http://www.eham.net/articles/2621 I have at least one of the dipole connectors, and have made some my self. Not hard to do. The dipole is rotatable, so it is directional and can be mounted on a short mast, which can be mounted anywhere.
I agree that the Outbacker is a very good antenna, but it is fairly long size, still requires a ground connection (most are used on cars and trucks). One other concern is to use a conductive non corrosive grease on the plugs of the jumper cable.
I did some experiments with the Cal 46, where I had 3 Ham Sticks mounted on a 3 way mount on my Radar Arch, which was 9' off the transom. The entire arch was part of my ground system which also included SS water tanks, about 70' of 3" foil thru out the boat, and Aluminum diesel tanks. I also had a large dyna plate which was just a bit foreword of the Radar arch on the bottom of the boat, which could be switched in. I had rotary switch so I could go from a single wire about 60 feet Stern to masthead--insullated, and not parallel to the back stay. The ham sticks, a 23 foot Shakespeare Marine HF antenna, and a inverted multi band tuned dipole--had to be put up and tacked or jibed, depending on point of sail--from bow, to under spreader (about 30 feet up) and to stern rail. Depending on band and propagation, I would gain 1 to 2 subjective S units when I added in the Dynaplate. (not sure that the drag from a Dynaplate would be worth it in a C Dory, but a flat copper plat could be put in (some issues, with the core and securing the plate).
Often the Inverted V Dipole would give the best signal reports, but nearly equal were the long wire (with tuner), the 23 foot Marine antenna, and the Ham Sticks. Often the receiving station could not tell the difference.