Unusual first legs:
Long - About 2,500 meters, at a one-day meet near Drammen, Norway, a week before the 1978 World Championships. I don't think I took a particularly good route. (The first leg in this year's Highlander was about the same length, but a mass start is different...)
Weird - Day 3 of the 1978 Team Trials in Minnesota (chosing a team to compete in terrain like that above!). The lake was dried up, but you couldn't tell if the muck was firm or soft. The start was set up so that anyone waiting had a clear view out over the "lake". I had a very early start, and like the couple of runners before me, I didn't want to chance heavy going across the lake. The women's couse was going the same direction, and Sharon started just a little after me. Sharon went straight. Apparently people timed her until she was across, compared to those going around, and -- everyone after that went straight!
Uphill - Day 3 of the French 5 Day in 1994, over near the Swiss border. The actual start was down in the field marked by the little red triangle. 11 lines up to the map boxes (a note on my map says - took 2:30 to get to start!), another 11 up to the first control.
Short and into the maze. Day 2 of the 1989 US Champs in Santa Rosa, CA. I've blown it up a lot. Distamce was about 120 meters. Description was "Middle knoll, west foot."
And the ultimate, the start in the wrong place, about 300 meters SSW of where it was marked on the map. Day 1 of the 1985 Convention meet, Smarts Brook in New Hampshire. Apparently the start crew, non-orienteering relatives, thought it was a prettier place than the spot they had been directed to! Lots of poeple had lots of problems (the forest was really rough as well).