There could be multiple diffrent reasons, and/or, some combination of reasons.

Here's a few guesses:

1. As mentioned above, perhaps Ham smeared us, and has their ears
2. Perhaps they only want one Canadian community, because the size of Omega's following, while large enough to justify its existence, isn't large enough to be split into two communities
3. If the mod teams from each community help fund the entire .win network, then perhaps Ham has been reliable in keeping up with the server/maintenance fees, and if they only want one Canadian community, as an unknown, FreeCanada creates some additional risk in these terms
4. The .win admins might simply not know us at FreeCanada well enough, and only want to work with people they know well enough to have a reasonable amount of trust in
5. Originally we thought that maybe they would want us to prove that we have enough of a base and are dedicated enough (being around for ~2 months now, this no longer seems to be the case)
6. Maybe Ham hasn't smeared us specifically to the .win admins, rather, his userbase on Omega (he has all of these screenshots to 'prove' they're all a 'bunch of racists' which he frequently trots out), and if the .win admin team hasn't really watched Omega (to see Ham's interactions with people there), they might take his word (with the screenshots) that Ham isn't the problem, rather, it is the userbase ... so, by extension, why allow another .win community which would have this same 'problem'?
7. Perhaps this has nothing to do with OmegaCanada or FreeCanada at all, maybe the .win admins simply don't want any new communities (e.g., apparently some members of IP2 wanted to form a new one, but haven't had any traction it seems)