I don't run Glitchless (at least not yet) so I could be wrong, but I'm fairly sure the program does not update automatically. You have to manually use it while playing.

you have to enter everything manually. Basically you check your stats on the lvls you enter on the right and then click on the button with this stat on the left panel. This elimintates impossible dv combinations. If you do this on some lvls you get your dvs. Red helper is not a super advanced programm that does all the stuff on its own, its more like a usefull tool to give you the information you need to make the right decissions :)

Therefor id recommend finishing some runs and getting a 2:00 atleast before using redhelper to understand the right decissionmaking with it.

If it did grab the information for you automatically, I'm pretty sure that would be considered a Tool-assisted speedrun, so that's why you have to enter things manually.

(The automatic updates would only work for those on Emulator. Everything you do during a run must be possible with the original console, otherwise you're using the emulator and/or some other software to gain an unfair advantage.)

I have not watched Pokemon runs in a while, but I'm guessing that they simply do it themselves... Just like hitting their splits. With Pokemon being an RPG, I'm sure there's plenty of time to hit a few numbers. ;)