It's based mostly on luck. Sometimes it works, most of the time it doesn't. Just don't press right or it kills your speed as you cross it, guaranteeing failure.
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I know about the whole pressing right slows you down thing in the air(it kind of made Sonic 1 slow by that happening when you where just running on the ground). And I noticed in your WW1 video, Sonic goes into his running sprites(the red "circle") at top running speed(without springs, speed shoes, ect.), but he uses his walking sprites when hes at that speed in the PC/SGC version(though he still flashes when you try to time travel, does that mean hes a bit slower in Wacky Workbench in PC/SGC? And in SS3, does Metal Sonic hit the door faster in Sega CD then he does in PC/SGC? I seem to get to the starting area before the "race" at the same time as you, yet Metal hits the door at the end at around 00:59:xx, yet 00:57:00 in your videos. And are the Special Stage UFOs placed differently in PC/SGC?
BTW, if I have any ?'s about SCD, should I PM you?