Since it is easier to hit the diagonals when using an analog stick and me fearing the games were designed with that in mind, I'd prefer that, yes. And since I'm moreover really not liking the stick positioning on the Dual Shock, I first need to find a way to play with a controller where the left stick is comfortable to reach for me.
Personally, I feel like the analog stick of the DS3 (we're playing on PS3) is wholly uncomfortable to use. I feel like that with the DS2 as well. You know, I don't know how exactly I was so okay with the DS2 analog stick as a teen. I really don't care for it all now, and it has me a bit wary of playing games like SOTC that are on my shelf, waiting to try.
I'm hoping any post-PSX Crash games worth playing are playable with the d-pad. Also hoping you can find a controller that suits your needs!