My 'vacations' are generally of the 3 day/long weekend variety. Those include the Friday before a holiday weekend--so I will definately plan way ahead, especially as I'm travelling solo and want to ensure that sometimes elusive upgrade. Right now I've booked most long holiday weekends from now thorugh Easter--with thoughts of IST for Memorial Day. I've found I rarely have a problem getting the upgrade when planning ahead, and as for hotels, I'll just book the cheapest showing rate (as long as it is cancel-able) and keep checking back for lower rates/deals as time gets closer.