The 92-93 Magic had Skiles, Anderson, and Shaq start basically every game. Dennis Scott missed about 30 games but was locked in as the SF. Anthony Bowie started the missed games from Scott/Anderson, but Tom Tolbert and Jeff Turner basically started at PF. Penny's 1st year they still had Skiles, Anderson, and Scott and Jeff Turner was the PF. They added Grant for 94-95 season because it was the glaring hole. In order to sign Grant they had to dump Skiles and did so with the 96 1st rounder.
So to me it seems like Webber filled a much bigger hole than Hardaway. Skiles was far from a great PG, but he was good enough and they could have gotten by with him (especially his great outside shooting). By making the Penny trade, they had to move Scott to the bench and to fill in the PF hole had to dump Skiles with a 1st round pick (which cost them a shot at Kobe/Peja/Nash).
I think the Magic would have been pretty darn good with Skiles/Anderson/Scott/Webber/O'Neal as the starting 5 with Turner, Bowie, and Royal providing some quality play and veteran leadership from the bench (that would have been 93-94 i.e. Webber's rookie year). Give Webber and Shaq a couple of seasons together and who knows how good they could have been.