David,
Most of my shooting is WA C/Y, so your issues are familiar.
Money. The C/Y used market (Ebay, KEH) is nicely priced and stable: all my lenses but one are 2nd hand. If you buy a lens this way and then don't like it, sell it for no loss.
Flexibility. Gearheads - like me - usually have more FLs than they ever use. Select one WA and see if your needs are met. 2nd-hand CZ primes, Yashica primes, or even a Tamron Adaptall zoom, will let you test the waters cheaply.
Weight. Distagons come in two weight classes: heavy, and heavier. I often settle for the D28/2.8 because the D21 is too massive for casual use. The only escape is use of symmetric lenses like Contax G or Voigtländer LTM.
Optical quality. Can't speak for the D18, but either D28/2 and D21 will make you happy. Stop down a bit, and light fall-off is unnoticeable.
And now, a spanner in the works: Architecture. This is a problem, the severity of which you must decide. As you can see from the MTF,
all Distagons have 2% linear distortion, and the D21 has the gull-wing variant for extra entertainment. You can see a fantastic write-up at
http://www.vanwalree.com/optics/distortion.html by Paul van Walree. The Contax G Biogons are better in this regard and, if you want to go crazy, get the Hasselblad SWC (CZ 6x6 Biogon extraordinaire).