Two tournament ones that still sting for unique reasons:
2010 vs. Butler - of course this is the year we got bounced from our expected #1 seed in the South to #1 seed in the West (Onuaku injury combined with the Dome hosting the East region)... so I bought tickets for the Sweet 16 in Houston (South region) and a plane ticket, given that an SU friend lives in Houston and it seemed like a no-brainer. Of course, we got moved to the West.. not all is lost.. the games would be on staggered days and I'd still get to watch some good games. Not so much. I landed in Houston, we rushed to a bar to watch the Butler game, and lost. Still had Fri/Sun games ahead of us, which were pretty much terrible knowing that our season had ended, and not even in the right city.
2011 vs. Marquette - went to Cleveland for this one with a friend who lives in Pittsburgh... so we 'commuted.' Did the Friday games too, and found out at the end of that session that we would have the late game on Sunday. Not ideal, since we'd be driving home very late to Pittsburgh that night. We lost. To Marquette of all teams. As we're leaving the arena through a side stairway/fire exit, we open the doors to the street and are immediately greeted by a monsoon. There's no shelter to even consider our options, we couldn't go back in the arena, and we were not dressed for the weather. The car was parked many blocks away. We drove 2.5 hours home soaking wet. Plus, I was holding great tickets to the East Regional in Newark, which I had to sell. I don't even recall making any money off them.