You should come visit me, I'll buy you a (free) taco or two.
(But yeah it is generally a pretty annoying holiday, I can't disagree there. I was actually meant to be born on that day, that'd be weird, but kinda cool.)
Unfortunately I can't travel from my slowly thawing wasteland to Australia right now. Gotta wait in agonizing indecision for a faint, likely imagined chance at changing my current conundrum.
Though I'd likely be able to actually interact with more people in person there than I'm able to here. Haven't been able to get a meaningful face-to-face conversation in months with someone my own age. The disconnect is really starting to get to me.
No, no, confessing your feelings on valentine's day way is more romantic, and maybe she'll be more inclined to say yes than if you had waited a month later. Hell, you really only have to go up to her at work one day *before* valentine's day, and ask her if she wants to get coffee or lunch with you on valentine's day, right? Maybe bring flowers?
Or maybe she gets 20 people asking her out on that day every year so you should beat the rush by a week, who knows. Certainly not me.
Maybe I'm being old fashioned. There are always flower and heart emojis. 
Your advice is certainly sound and if I were in any other scenario than the one I'm in I would most certainly follow it. I know I could set up something appropriate even with this short amount of prep time before the holiday. Unfortunately, my circumstance makes that a no-go. I do appreciate the advice, though.