Well, my T1i is still going strong.
From what I understand, the 60D might help with focus, which appears to be the problem here. But I would rather invest in lenses which will make even that seemingly poor-performing camera work better, and not get frisked for cash every cycle when buying a new camera - if you're interested in candids you might like a faster prime...I'm guessing these are taken with the kit lens? (I sold mine straight away so I have no idea what it's like). Ideally, you'd be able to get the 50mm 1.2 to duplicate that sharp-but-not-unflattering look you're aiming for, but the 50mm 1.4 seems to be good enough in my view (plus on APS-C 50mm is too long for close quarters shots unless you're just going for head and shoulders portraits). I've taken a couple good portraits with it in lower light.
The 60D's focus system has rave reviews, but those like Osiris posted are using better lenses. I would think that if you're just going from one camera with the 18-55mm consumer zoom to another, you might not see nearly as big a difference as getting a better lens. If I were you I'd get the 17-55mm f/2.8 EF-S and save on weight, and just use the center dot for focus. Or you could save a lot of money and just get a faster prime lens.