A FlyerTalk Posting Legend
Join Date: Jul 2002
Location: MCI
Programs: AA Gold 1MM, AS MVP, UA Silver, WN A-List, Marriott LT Titanium, HH Diamond
Posts: 52,575
Usually book in advance if flights/hotels are involved. I used to be a big fan of the weekly "netsavers" type emails for close-in trips, but those emails haven't had attractive airfares in them for about a decade.
If it's a long trip, I'm probably looking for J/F seats and very good hotels. Thus I'm booking early to get availability - often for 2 or 4 seats per flight. I've found that the old 330-day rule isn't as applicable anymore, but planning 6 months in advance is helpful to finding good routes and dates.
If it's a short trip or one where I'm just looking for cheap Y tickets and unremarkable hotels, it can be in the 6-8 week range assuming it isn't a peak travel period.