I imagine a scenario where the original poster is compelled to roll back multiple edits to his post, causing it to become a community wiki, thereby losing any future rep points from that post.
Can this happen presently?
Should this happen?
Rollbacks do not currently count at all towards pushing a post to Community Wiki. This was tested way back in August 2010 and still holds true today. They certainly count as edits for the purpose of existing in the post's revision history, no matter how many you make, but for the intent of converting a post to Community Wiki, it is as if they never existed.
Revived the tests today just to confirm that nothing changed. And indeed, nothing changed. Thresholds still are the same, and the post remains completely unconverted no matter how many rollbacks happen.
As for whether or not they should, I'm fine with the status quo mostly from the perspective of "Don't need to fix what isn't broken" - it's been this way since the dawn of the system and there's been no widespread inclination to abuse it. Abusive use would thus be the outlier in the statistics and so that should be the "exception" that is handled by moderator intervention.
Yes, rollbacks will count as an edit, and add to the total required to auto-convert to Community Wiki.
I don't think they should work that way, but that's present behavior.
Yes rollbacks count as an edit.
Yes, it's important for it to stay this way. One of the main reasons for CW-ing a post that has been edited a lot is because editing a post bumps it to the top of the "active" list. Some people try to edit their own post a lot with trivial edits to keep it at the top of the list (to try to get more upvotes). If a rollback didn't count towards that then a user would be able to keep rolling back their post between two previous versions to bump it indefinitely without it ever becoming CW.
If a post of yours becomes CW as a result of a number of improper edits from other users, flag the post for moderator attention, explain that it became CW because of the inappropriate edits of others, and they may decide to un-CW the post (they can do that).