Yeah that's a nice idea. Perhaps it requires a website, to coordinate such world wide effort, and code an easy way for participants to submit their finding.
Was also wondering: could short wave radio be used to measure distances? There'd no doubt be a bit of variance from atmospheric conditions, but I'm thinking the precision would be less than using flight times/plane speeds. Would also require a large amount of coordination, and not many people have short wave radios... might be able to get the SWR community interested though. I wonder if internet calibrated clocks would be accurate enough. Apparently light circles the earth about 7.5 times a second... the cities i've chosen (and can be changed) are roughly 60 degrees apart, so light/EM radiation would take about 22ms to travel 60 degrees (plus a bit more once it goes up, bounces of ionosphere, bounces back again). That's reasonably "slow" in the grand scheme of things but maybe the combination of clock accuracy and atmospheric conditions would make the data essentially useless hmm
Another method i was thinking of: we have access to a huge database of images of land (i.e. google maps). If the "great round earth conspiracy" is ensuring that google map images are stretched or skewed away from flat earth "reality", this can surely be measured using known lengths? We could use cars for example: you could get an average length of a car, and use that to "calibrate" any google map image, or confirm that the image isn't being stretched or distorted. If you've confirmed it hasn't been stretched or contorted, you can also use the same cars to provide an accurate length of distance for each image... Do that enough times from place to place and you have a another method of measuring distance. Again, a lot of margin for error in such a calculation, as most google map images only have a resolution of half a meter or so, plus relies on populated land between each location. In order to prove the globe earth I think the most useful distances will be between Africa, South America, Australia, and pacific islands, so that makes that a bit useless.
Or we could of course just use "known driving times"... You can use google street view to get distances from signs: gather enough data, they can't ALL be wrong...
Or use shipping distances and times: but as we've seen on this site, direct evidence from people on board such ships is tossed aside.