It would make sense for the stage 2 100 octane car to pull you to 95 and you creep afterwards. These cars are terrible once they shift into 5th gear.
It doesn't take a WGA to get to 105mph. I know somebody on Golfmkv that did 105.9 mph on APR stage 2+ with a stock BW K03. He had catless DP, BSH FMIC, air intake, etc... He switched to Revo with the SPS+ and ran a Forge WGA and then got the 107.x mph trap.
Just on my set up with the mods in my sig I'll run my friends C5 from a 40 roll with me in 3rd and him in second and only lose 3 cars to 110mph. If how you beat VW's in the past is indicative of how you'd run me apparently you're LS1 fast? I doubt that and I'm not putting down your car, it's impressive for an NA Honda set up. I believe you should get a better platform though (I posted that on Golfmkv).
From my experience, on the street anything can happen. My friends C5 barely edged a full exhaust, tuned and intake EVO 8 MR so I know his car is fast. I've also noticed some cars run well and some don't. I think a lot of it has to do with miles, maintenance, driver and the amount of options the car has affecting the weight. As an average though stage 2 FSI =101-103mph, stage 2 TSI/stage 2+ FSI = 104-107mph. Some cars don't get anywhere near those traps but the good drivers in the right cars will always get in that range.
As far as trap speed not meaning everything, it does. From a roll it's the biggest indicator of what's going to happen. If its from a stop, totally different story.
FWIW, you running MKV/MKVI's from a 40 does not give you a good idea of how the car runs. It takes away the GTI's advantage and favors your set up. If the stage 2 100 octane car had proper summer tires or DRs and you ran a 20 you would've never caught him AT ALL
It's a moot point arguing my point because I'll never get the opportunity to run you from Florida but I figured I'd tell you what I've personally seen down here.