To add insult to injury, it seems like he just blows me off, like he's not even really trying. He still gets me in the same areas, because apparently there's not enough time to dodge his strikes.
Hate to tell you, but he's probably not really trying. As you said, he gets you in the same areas every time, so it's almost become rote for him. You can change this in several ways, the least of which is to at least force him to attack/hit you somewhere new.
The most BS part about this is that Even when Im close, he STILL somehow gets out of my reach or hits me first, and its almost impossible to hit him first since he can predict where I can hit him. This is because the way he holds his huge fricking crossguard narrows down the number of areas I can actually target to a few specific areas.
No, he can predict where you're going to attack him because you always attack him the same way.
I know people keep saying that the crossguard saber isn't that much of a monster, but in this case IT IS.
No, it isn't. You're angry and frustrated that you haven't got past it yet. And you probably get angrier and more frustrated every time you lose, which makes it more and more likely that you'll lose. And your opponent knows all of that, and knows what he's doing.
So yeah, even though I'm trying my hardest, my ass is constantly getting beaten and I'm getting increasingly frustrated because its always like I'm just a nanosecond too late or less than an inch off.
What the hell am I missing?
I'm going to refrain from the obvious answer to that question. I'm just going to mention in passing that, while a nanosecond difference will win you a match in Kendo, in a battlefield situation, or even a duel, that small of a difference usually means both people die.
I'm trying whatever I can that's within the bounds of my club rules, with no true results. Do I seriously have to BUY my way to victory by making my hilt longer? Or am I just not gonna be able to find a way past him with single blade?
As much as I'd like to answer both of those questions with a "No" I realize that I really can't. If it were me, the answer to both would easily be "No" but you're not me. I don't think you'll have to get a longer hilt, and I think you should be able to get past him with a single blade. But like others said, that's harder to tell without actually seeing a match (like the others above me said, get us a video!). I know what my first dozen or so attempts would look like, although since I haven't seen him fight, I have no idea how successful they'd be.
Quick question, what does his starting stance look like?
I do like janx's advice on fighting defensively (at least in this case, not something I normally do). It sounds like you're the aggressor and he's simply dealing with your attacks. I'm curious to know how it would go if you forced him to attack first.
If you don't think you can beat him, then you never will. Speaking of which, one of the things I love reading here on the forums is people's signatures. Some are really creative, or at least pretty good. One that I read recently had this in it: "There's nothing, no opponent I cannot beat (eventually)."
Yes, I know where I read it.Very last thought: Obviously he does very well within your club's ruleset. I just wonder how well he would do outside of those rules.