Hi Sean,
unfortunately I own neither of them, because I concentrated at "late" lenses in my collection except my 1.5/50, which is from ~1955. I would be curious to compare the Canon 3.5/25 against the new Voigtlander Skopar, but not enough to pay 500 USD for the lens... the 3.5/25 is well reputated, but I cannot imagine that a prewar Zeiss Topogon derivate will beat the Skopar, which all cites as one of the best wideangle lenses ever designed for Leica screw mount...
Another thing is the rear element of the Canon, which some sources like Canon museum say it's a flat glass (center filter), some deny... I suppose the last series has the center filter.. without it a classic symmetric design like the Topogon will create huge light fall-off...
As you probably know from Canon museum, the 3.5/19 comes in two designs, one small and very deep, two was a modified SLR lens with big front element (Canons first retro-wideangle and as sources say better performer than the first one). I don't see the point buying such a big lens having such a small and excellent lens like the 4.5/15 Heliar in my journey case.
The 1.8/50 is a fine lens. Optically the Serenar/ brass and later "black-chrome"/alloy are the same- I had a late one which I sold because I'm so happy with my 1.5/50, a "classic 7-elements/ 3-groups Sonnar design" when the 1.8 is "another boring Planar type"
Maximum contrast isn't always required, that's I agree to you. Some high contrast motives attain if the lense is not too contrasty, in particular in bright sunlight or with slides film. But not this kind of softness coming from a lack of optical corrections, leading to a dull image in this kind of motives... overall, I would encouarge you to compare the Canon RF lens line with the new digital RD-1. The older Canons don't belong to the last class.. in particular the late series: 1.4/50, 2/35, 1.8/85, 2/100 (as well as the older 3.5/100) ... and, yes, the "monster" 0.95/50...

as far as I know, the 2.8/28 is also one of the latest. I don't have it, and Peter Dechert denies its quality in his excellent book, but who knows... as far as I'm concerned (as a user) I have a hard time deciding which lens I shot when getting the pictures back... all excellent up to 10x enlargement...
cheers, Frank