I thought about using the miles to buy a ticket to Boston for SMOFCon. Unfortunately, even this far in advance, the number of flights on which I could actually use the miles is highly limited. I had hoped to fly from the Bay Area on Thursday, December 6, possibly on a red-eye so I could avoid having to take that day off from work, and fly back on Monday, December 10. The only combination that I can buy for 25K miles (the lowest level) not only requires me to take December 6th off (Lv OAK 9:30 AM, Ar BOS 11 PM, via PHX), it requires a very late flight on Monday the 10th (Lv BOS 8:19 PM, Ar OAK 1:34 AM next morning, via PHX), which would leave me in less-than-good shape for working the next day.
All of the other combinations of flights require a minimum of 12.5K more miles, which is more than I have to spend.
So I opened up the search to encompass San Jose and San Francisco. Here we get some more useful possibilities, although they still oblige me to take that extra day off because the red-eye is never available for the lower price.
Flight calculations also have to take into account having to be at the airport so long before the flights. This is why I try to fly from Oakland whenever possible. It's quick and relatively easy. Getting to SFO on BART is possible, but it takes a long time because it's "long-way-around" -- possibly the longest single trip you can make on BART. For example, I can book a flight that leaves SFO 7:00 AM, arriving BOS 5:49 PM (via CLT), but the earliest I can possibly arrive at SFO on BART is 5:21 AM, requiring me to take the 4:20 AM BART departure from Fremont. Ugh. And while 90 minutes early is usually enough, I always feel more comfortable getting there two hours early. At least the return is nowhere near as ugly; A 12:35 PM departure from BOS, arriving SFO 6:20 PM (via CLT). Depending on how fast my luggage cleared, I would be back in Fremont by about 8:30 PM.
I guess I'll use the miles to book the ticket, even though it costs me an extra day of time off and a hotel night. But it's still a free flight that would otherwise go to waste and I will have the time off available, even after soaking up over a year's accumulation to go to Japan. And aside from having to be up insanely early for the outbound leg (leaving the house at 4 AM), it does mean I'll not be rushed for time at SMOFCon either arriving or leaving.