Hey I've never had any problems going upwind on my skater.
Which skater are you looking it?
The new 5'9'' is super fun. They narrowed the nose, which was needed, made the deck flat, very interesting feeling, and the rail is a little straighter, with a tad more tail rocker it comes off the top very nicely. Good times.
If the main concern is upwind maybe the global line is a better choice? It has a 5 fin boxes..I think the rails are a little straighter on that board thought 2013 skater is getting there..
I do not know anything about the firewire, but it is probably a good board too.