Well, firstly, you didn't mention the state characters would be fighting in (part 1, part 2, FSWW, post-FSWW etc). But I think they both have condradicting skills anyway. The analytic mind and tactics are Shikamaru's advantage, but, unlike Lee, he lacks actual fighting prowess (although I cannot say he's powerless completely), so he wins his battles mostly with his mind, not sheer strength, which, again, is Lee's way of settling the things. I know it's pretty hard to come up with a strategy against 8 Gates, but still Shikamaru should take it.