Hello all -- so, I'll throw my two cents in here, although no one ever offered me more than a penny for my thoughts! LOL.
First, bottom line, I think overall it's much easier today. I hate being generic, but that's my opinion. I've played for the better part of 50 years and started out playing on bar room tables and went on from there. Playing on the nap cloth to me was like playing in the wind. Like quicksand. Sure it was challenging, you had to know the table and so on.
Second, when I talk to younger players today who say it's "tougher" today -- most of the time after drilling deeper I find they are mostly talking about smaller and tighter pockets. Sure, that's one narrow topic where of course it's tougher. Personally, I like playing on smaller pockets. But it's the tight, very tight pockets that add another dimension of complexity. Even without looking to cheat the pocket, you have to know what's falling and what's not.
Also, I think some of us -- us older guys -- think about when we were playing as kids (yes, back when we were in our 20's and 30's, LOL). I don't know about you guys, but I started with 8-ball, played a little 9-ball here and there, and graduated to straight pool. Years later I got into 9-ball more seriously. Today I play one pocket and that's all. Back when I was a kid it was about sledgehammer breaks and banging balls. Totally different game.
So we are comparing different games with totally different equipment. Regardless, to me, it's easier today. Especially if this is what you were brought up on.
Very good thread. Thanks everyone.