It's been awhile.
Ryan, if you're gonna lose sleep over it, get it over with and just ask her. But if you'll be fine without knowing how she really feels, then don't. Don't set yourself up for possible heartache unless you feel it's worth it.
Now about your new strategy, well... it's safer than outright asking, but then that sort-of puts her on the spot. If I were her, I wouldn't know what to say. It would be like, "Okay... what am I supposed to say after this guy tells me just how much he likes me and I don't feel the same way?" And if ever she DOES feel the same way but has her own life, she still cant give you a proper response. So if you can't expect her to be fully honest with you, even if you change your style, everything from her end will be the same banana. Therefore, when in doubt, don't.
Besides, lots of other fish in the sea. Especially when you get to college.
Go for someone who can actually see how special you are.