My 2 cents on the timeskip, even though no one asked for it. :)
I agree that a timeskip would be convenient soon as more players end up 'going to sleep' at the end of night one, however I would strongly request we don't immediately jump to the boss battle/pre-boss planning. For one, if we're following a loose timeline of the show it took over a month to discover the boss room on floor one and I personally think a month is a bit too long of a skip. Secondly, I like the idea of this RP being more focused on actual every-day life in Aincrad rather than the progression through the game, as the show portrayed, and would certainly welcome more time to level up, develop characters, discover 'secrets' and the like. Would be fun if the GMs, or even other members of the RP, started a sort of 'quest board' that our characters could use as an excuse to team-up with each other (when they wouldn't otherwise meet).
Perhaps if we were looking for a way to get everyone together in 'the same room', as it were, there could be some other type of large event/rare group quest that would draw the players together. I also liked the idea of someone starting a guild that willing characters could join to provide more opportunities to act within our already-forming groups and the wider 20-something of us that are part of the RP.
The guild thing could start a ways down the line though, I'm in no rush (neither is Geist).
Jus' ma thoughts!
Taking into account there are a total of 100 floors and the giga bosses every 25 levels, I don't think time skipping to the start of the level 1 boss fight is that big of a skip. The idea of rare events/group quests like you said won't be something thats available on floor 1. Remember the fishing hidden event?
These sort of things open up the further into the game you play because people start diversifying their skill sets (e.g. fishing/smithing/cooking) into advanced levels. Stuff like our characters hunting and enjoying searching/cooking a Ragout Rabbit seems to be along the lines of what you're talking about. But these things won't appear on level 1 nor would they be the type of thing people do several days into the game because people will be either despairing or focusing on clearing it.
I don't have a say on the time skip since I'm obviously not a GM but I wanted to explain to you how procrastinating on level 1 won't get you to the scenario you're describing. In fact, I don't even think going through 100 bosses is feasible. We're bound to enter periods where we're bound to skip several floors at one go or be forced to have go through repetitive boss fights which some people might like but I'm rooting more for a interaction roleplay and not grinding as if it was a real MMO. I mean if I wanted to then I would go play a real MMO.
Btw I'm discussing and not shooting you down or creating a fight or anything >_>.