RE: Help with board
The S-Type 115 woould be my suggestion as a replacement for your Seatrend.
The S-Type has all the things you seem to want.
It's pretty fast, jibes pretty well, handles chop well and really like fast back and forth reaching, but it will go upwind fairly well also. The stock fin is pretty good, but mine spins out some, so maybe a fin upgrade and you should have an easier to slog board that's as fast (if not faster) than your old Seatrend.
It almost sounds like a wider board (Isonic perhaps) would be better at planing early and slogging, but I'm not sure you are ready for such a giant leap in technology.
The Carve 111 or 122 might also be worth considering.
Hope this helps,