I think Shaq with just about any mix of NBA-caliber players would eventually win a championship.
Sure Hardaway along with workhorse Horace Grant (who wouldn't be there with Webber) were great fits next to O'Neal, but this is Shaq we're talking about, how much does the fit really matter as long as Shaq dominates? Remember how weak the East was during Shaq's time in LA? Very similar to LeBron's cakewalk to the Finals now.
So to me, the only question here is, does Webber on the Magic keep Shaq in Orlando? From the recent "Magic Moment" 30:30 special, as well as reading some of Shaq's books in the past, it seemed Shaq and Penny didn't get along too well after Penny became a superstar. Also Penny got a new contract first, and Shaq says he went to bat for Penny telling management to pay him, but when it was time for Shaq's contract, Penny didn't do the same and that helped push Shaq out the door.
With Webber taking a while to find his groove (being injured in years 2-3), as well as being nowhere near as marketable as a prime-Penny was, I could see that being enough to keep Shaq around. Shaq wouldn't be threatened by Webber's star power and media presence (or lack thereof), and ironically maybe less success in Orlando in those early years may actually have made Orlando more willing to pay Shaq. With Shaq, Penny, and a Finals appearance in the franchise's 6th year, management might think hey this is easy and we'll be okay as we still have Penny and a good team. But with Shaq, an injured Webber, and no Finals appearance, maybe Orlando's management is more willing to pay to keep Shaq, maybe building a successful team doesn't seem as easy to them?
So does Shaq go to LA no matter what? If Orlando offered him a huge contract upfront does he stay? Does playing with different teammates keep him around? If anything keeps Shaq in Orlando, then Shaq would win a championship there, whether it's Hardaway, Webber, or Shawn Bradley.