The pitch of the props you would want would be that which will allow the single engine to achieve rated Wide open throttle. I would want a prop with the pitch which would give about 6000 RPM. If you have both right rotation engines, then one prop, would be satisfactory. If you have counter rotation engines, then you want two props; one for each rotation.
Since the origional poster was getting 4400 PRM, He could drop the pitch of the prop considerably--at least by 4", and maybe 6"--but then you want a "big foot" prop, to utalize a larger diameter prop, which will be more effecient.
There is no real "magic" number for displacement--but the 1.34 is usually the number touted for a real full displacement boat. One that will not go any faster no matter how much HP you apply. At least one of my sailboats quallified in that category--it would go aboout 9.5 knots at WOT--I had 90 hp, some of the sisterships had 130 hp--they all would go 9.5 knots max. This was because this was a double ender under the water, and there was no lifting area in the boats aft buttocks area (nautical term).
As you applied more hp, the boat dug a bigger hole in the water, but went no faster.
The C Dory is a different type of boat--since it has an essentially flat bottom, with a little rocker, it has a lot of lift, and will run at a semi displacement speed, right on up to a planing speed, with a modest amount of HP. Now, if you were able to develope the max hp (and torque) for the 50 hp engine/prop combo, it is entirely possiable that you could to 11 knots--or maybe 12 knots--but do you really want to run that engine at WOT, or near it, when the other engine has failed?
I had done a comparison of the Tom cat 24 and the Glacier Bay a couple of years ago--and Georgs reminded me of in a private post, unrelated to this thread. I had noted that the Glacier bay (a semidispacement cat), would go up to about 15 knots, and the Tom Cat (a planing cat) would not go beyond 9 knots. There are boats which are built to be semidisplacement boats--for example the Rosborough 246--and it probably will go faster with a single 50 than the CD 25 will (I haven't checked the exact speeds, but I remember some posts from the Rosie list suggesting that). It has a different hull form.
Keep in mind--that your 9.9 may drive that boat in flat calm water at 7.5 mph, but it will not in winds or head seas--were as the 50 will keep pushing the boat at 9 mph in head seas and wind. I am personally willing to accept the lower speeds with a kicker, but some people want the greater margin of safety.
One also has to analize the failure of modern outboards. Most likely it will be fuel related. If one engine is getting bad fuel--what is the chance that the second engine is? For that reason, I like to have a separate tank for the kicker. The other more common failure, is that the batteries run down--and then both 50 hp are out--I have never hand started a 50--but I used to hand start a 40 (before electric start was standard)--so it is possiable--at least when you are younger. Also the isolated back up battery is a very good idea, so that if you run down both batteries, you can still start the engine.