, but I can't say I still quite "get" what I should be looking at or looking for in my first board. I've been boarding a couple times, ridden the Burton LTR, Cruzer and some Rossignol board
You've obviously done your research and you've ridden a few boards. Kudos, you're way ahead of the curve.
If you can tell the difference between the boards you've ridden, but find that you can't do some things on one that you can do on another, I'd really suggest you invest some moeny in lessons. No offense, but no board will "prevent" you doing anything (except maybe catching an edge on rails/boxes)
I know that sounds pretty pompous, but think of it as research. You're prepared to drop a lot of coin on a setup, make sure that you don't buy a board that merely compensates for today's riding style but not next year's. I've got a friend who rides totally counter-rotated and always skids his turns. You can't tell him anything and he spends money on boards like it's going out of style. Always looking for that perfect combination of edge bevel, sidecut radius and flex that will allow him to carve prefect turns. Well, duh...it's not the board!
Without anything to compare it to, it's going to be hard to make the choice on spec's alone. I have no idea what the flex rating of my board is, I'd have to look it up and even then, I won't know if that number is comparable from brand to brand. But I can tell that this board is softer or that board is stiffer when I ride it.
Maybe buy a cheap board (or rent something you can get spec's on) and learn what you hate/like about it? Then you'll know that you want something longer than this, stiffer that that, wider than this, etc.
You're obviously prepared to invest time and money and getting the perfect setup probably isn't going to happen on your first purchase. You'll probably be buying another in a few seasons.