As you can see, Peter, you're not going to get anything but love for these airplanes.
Although I own an original Cruisemaster (the 14-19 was the last aircraft made by G.M. Bellanca and his secret army of Sicilian craftsmen) and have nothing but love for its Lycoming O-435 engine (you can get a bit more than 190hp with high compression pistons), Lycoming has nothing but amnesia for this overbuilt hunk of heavy machinery (it's an orphan). After having it majored last year and playing find-that-part, I cannot recommend this travail to others.
Mine is more a personal decision than a practical one. Heck, no aircraft owner can truly say their decision was practical, although they'll try....with their non-pilot friends, family, and just about every stranger to the world of three dimensions.
In short:
Cruisair - the most nimble of the line and if you're fortunate enough to find one with an Aeromatic prop, it's also the smoothest and quietest of the lot. The only aircraft engine I've ever heard that is smoother than a Franklin (one sweeeeeet engine) is the OX5 - the Rube Goldberg sewing machine, as I like to think of it. The downsides are simply typical of the era: small cabin, hand crank gear actuation (37 turns to raise or lower) and a lot of neglected junk on the market. This is true for all old airplanes and certainly applies to the models below.
14-19 Cruisemaster - larger, faster, can carry more, aileron actuation via rods rather the pullys, hydraulic gear and flap actuation (I like the manual flaps of the Cruisair better), more horsepower and a controllable pitch prop. Downsides: orphaned engine that also tends to cook its cylinder heads, venturi powered instruments (a plus for some but not ideal if you're taking off with the notion of filing IFR to penetrate a low cloud or fog layer) intense cabin noise, a prop that you have to adjust (controllable but not constant speed), plus an expensive AD on that prop. Anything on the market now will likely have had the AD done, plus the replacement prop clamps are truly heavy duty.
14-19-2 Cruisemaster - same airframe as the original, but with more modern systems: more powerful engine that remains in production, engine driven vacuum system, constant speed prop, 200lb gross weight increase, and a more reliable (and still available) power pack and fuel pump. In cruise the two types are pretty much the same, but the -2 climbs like the Dickens. Downsides - no objective ones.
As for your question about a George, both Cruisemasters have STCs for the several early ones, but the only one still being manufactured is the Brittain system. Mine has only the wing leveler, but you can add components for tracking headings. This single axis system does not offer alt hold. It works great but it adds FIFTY pounds in servos and such.
Finally, there were only two hundred Cruisemasters made, split pretty much evenly between the 1950-51 model and the 1957-58 ones. OTOH, 650 or so Cruisairs were built and are, thus, more available.
Jonathan