I used to LOVE Strava and going for CRs on segments. It was the perfect competitive add on to road racing - no cost, you can run whenever you feel strong, and you can immediately go back for a second chance if you fall short.
Last year I set a Strava CR on a massive hill in a pretty populated area. A few days after I did, the guy whose CR I beat had gone back and beat my time by a few seconds. Fair enough, I thought. Strava has the tool where you can compare your pace on segments with the CR holder, so I looked to see where I had lost time. But strangely, my pace was faster than the CR holder, which didn't make any sense. I looked a little closer, and this guy had purposefully started the segment about 15-20 meters after I did and stopped it about 15-20 meters short of the top of the hill. GPS is imperfect, so the segment still registered, even though this guy had cleverly skipped between 30-40 meters of running.
To confirm I wasn't losing my mind, I re-uploaded my Garmin file to a new Strava account and "cropped" my run to match this guy's abbreviated segment. Sure enough, my time was faster, and I was again the CR holder.
At this point I realized just how ridiculous "digital racing" is in comparison to actual competition. I literally set a record days after having run the segment by cropping my run file. This was in response to a guy who had short cut the segment, knowing there would be no repercussions. Real road racers would laugh at this type of BS.
And "let's see who can run the most miles" contests are ridiculous. The purpose of training is to run faster races. Period. Running a fast 20-mile tempo run is pointless if it means you'll burn out for your actual marathon.