I booked mine about 6 months in advance (as my wedding is the weekend of the CWS) to make sure that I could get a block. I'd say anywhere from 4-6 months should be ok. And when you call they should be able to recommend how many rooms to block. Usually they start out with either 5 or 10, and if all of those rooms get blocked off then they'll add more to your block.
I would suggest blocking rooms at 2-3 hotels (depending on how many OOT guests you have) in different price ranges. HTH! GL! =]
I would ask your hotel that you choose and make sure nothing is going on that weekend. We thought we were safe but found out state track is the same weekend as our wedding, so hotels were getting booked already last March! I asked the hotel event coordinator how many we should block off and let her decide, then if we go over, they will add accordingly.
"The best thing about loving and being hurt is that you get to know what true love really is. For as gold is tested in fire, and so will love be perfected in pain."
Planning Bio/Blog
I would recommend calling around to different hotels as well. Some of them make you pay for rooms not reserved and some are no risk for you at all. We will be reserving with a hotel (or two) where if they don't get booked by a certain date then they just fall off the block basically. Does that make sense?
I used to work for a hotel and I don't recommend blocking at numerous hotels to give them different price points. If everyone but one couple books at the same hotel, then they may stick out as not being able to financially afford a better hotel. They also are not at the same hotel as others for getting together with others for breakfast, after hours things like hanging out together and such. You're better off to have them all in one hotel and if they can't afford the one you chose, I'm sure they can find their own hotel if need be.
As for on goings at hotels. If they have events on the books at the time you call then you may be aware of what's going on as well in the hotel and how many rooms they have left in case you need more. However, you can't control groups that book into the hotel AFTER you've booked. It could be just as busy either way.
Re: Hotel Rooms?
I would suggest blocking rooms at 2-3 hotels (depending on how many OOT guests you have) in different price ranges. HTH! GL! =]
Planning Bio/Blog
Most hotels don't seem to hold you for the difference but it's good to check.