I hate mechanicals on the bike

I've had a rash of "mechanical" errors on the bike in the past 2 months. Most of them were due to a rear tire issue because I had broken one of the screws on the frame, but on my weekend ride, I had a flat tire, which required some careful navigation and stopping on a screaming descent with cars to not wipe out. Fortunately, I made it through that entire 70 mile ride without any further mishap, and since changing my frame screws, my rear wheel is working great.

Fast forward to this morning. I got onto my bike and out the door at 6AM to join the LaGrange bike hill sprints this morning at 6:30AM. Keep in mind it's pitch black right now at 6-6:30AM, so I've got a headlight, rear blinkers, and am not really enjoying myself at all yet because I absolutely hate riding my bike in the dark due to safety issues.

The ride got started fair enough, and less than 1 mile into the ride, "BAM!" I hear a huge sound like a big balloon popping, and my front tire immediately goes limp. This was at first just a minor setback for me, as I figured I could change the tire quickly and rejoin the group on their 2nd-4th loops. However, as I pulled off the tire, I noticed one of the edges had run ragged. I suspect that I improperly mounted the tire on my last flat episode, and then my brake pad probably wore it down until it popped. Major bummer - there goes a fairly new $40 tire and a $3 inner tube.

So as of now, I seem to be "cursed" whenever I join the LaGrange ride, as I've managed to complete zero of the last THREE outings I had with them on weekday mornings. I don't know whether to be sad or glad, as I most of these mechanicals have been significant ones that immediately ended my ride, and these weekday rides have meant I've been close to home or my car. On today's mechanical, the torn tire meant that I lost complete use of the front brake since the front tire was bulging, and thus I limped home on the rear brake alone, which is much inferior on road bikes and definitely not something you want to do for more than 15minutes. If I had suffered similar mishaps during my long weekend 70+ mile, 5 hr rides, there could have been some serious problems along they way. But so far, no major problems on the big rides.

I think I'll be able to solve this problem quickly once I get a new tire and inspect the wheel a final time, but lesson learned for me - after a road flat, be very careful about remounting the new inner tube and tire, and then recheck the mount a second time at home in a more controlled environment.