My group and I ride the L.A.T.E. ride every year, this was my 5th year. We always end up getting in the first wave, right behind the VIPs and take a liesurely ride, we still end up close to the two hour mark. This year's ride was a new route & a earlier start time. The combo caused some level of confusion and I noticed a lot more upset motorists this year.
As for the lakefront path, it's always sketchy there. You really need powerful lights on that path, it helps. Luckily I've had no mishaps to date. I hope your friend heals up quickly Megarot.