The logic to choose the 66 over the 69 because it's a yeoman caliber, with a proven track record is inescapable. However, logic is what we use when we tell OTHERS what to buy...deep down inside, gun purchases are like new girlfriends...we're not sure exactly why, we just gots to have her!
I like the .357 magnum (who doesn't really) because it can do just about everything...actually, with the right loads, in the right hands, it can do EVERYTHING anyone might need. Time was, the .357 Magnum was "exotic"...the new kid on the block with brute power beyond anyone's dreams. Short barrels and liability loads have dimmed some of the aura, however those who load their own know the potential. A point in favor of the 66 is it's about well balanced for the cartridge as possible...it's not really built for a continuous diet of the hot stuff (but how many shoot that much hot stuff), and it's compact enough for general, all-around carry - even field carry.
On the other hand...the 69 is that new girl...with the exotic looks, with the allure of something wilder than you've ever known lurking behind smooth lines. A .44 Magnum in an L-frame is NOT to be dismissed lightly. Why? Because it TOO is an all-around performer, with known "street cred" as to its ability to settle the hash of the baddest of the bad. Five rounds is only one less than six, and for that sacrifice you get a much slimmer gun...not as blocky and chunky as the "old gal," but sleek and bulging in the just the right places to just the right amount! The L-frame .44 magnum probably isn't meant to take a daily beating of hundreds of full-house magnum rounds, but then who shoots like that? Nobody who's paying the freight for their own ammo and guns that's for sure. MOST who shoot a lot of .44 "magnum" ammo tend to load their own and tend to load a bit milder than top drawer, but whatEVER "they" do, it's what YOU do that counts. I personally find the notion of a "slimline" .44 magnum quite appealing...but then I've been "going to see the varmint" since I was 16 and don't seem to have enough sense to stop now.
Prices being equal...I'd buy the 69 today, tomorrow, next week, next year. There are a LOT of "Yeoman" .357 Magnum choices around...how many L-frame .44 Magnums? A handloader can dial the big cartridge up and down to suit...from mild to wild...and any way you slice the donut, a 240 grain hardcast SWC at 900 fps beats a 158 grain hardcast SWC at 900 fps. A 240 grain JHP at 1250 fps beats a 158 grain JHP at 1250 fps...and so it goes...