I believe it would require an add-on for this, but the skill pages on the wiki could still slowly be converted at a normal wiki user's leisure.
This allows lots of things though like letting you show all skills on one page without much hassle (roll-over), a 'build' section for each game so that people can easily show off a build without having to either type it all out (reading those is a pain when it's in plain text) or go use a simulator (that are often a bit off or based on another version).
I'm not sure if it's possible to also make the skill_db files editable wiki files, but I'm sure that with a little tweaking it should be doable, in which case if you make it editable by only people of a certain group or higher (VIP, Sysop, etc?) it can be taken care of without needing to be done by (I'm going to assume) very few people who have access to changing server files around.
To answer your question, from what I understand no current database has to be changed right away, you would just be adding this database for now, and then we would be moving over skill pages to reflect changes. There are a few games with skills either all thrown together on one page (and a lot of them) or not finished yet (going to guess only Dragonica as of speaking, the rest should be done so far) and it would be slightly easier to have this done and then toss them all on one page.
I'm not sure if this also directly allows the use of overLib through this, but overLib is nice to have on almost any database (personal opinion), if used correctly.