I'd say at this point, my top three pieces of equipment would be (not including my X-Challenge):
Firstgear Rainier Jacket. I wouldn't call it perfect, but I would say it is an excellent jacket. The fact that I got it under $150 (closeout) puts it over the top.
Grip heaters. Honestly, I don't think the brand matters or whether you go heated grips, under grip elements, or heated gloves. But having something to warm your hands does wonders to improve the riding experience and extend the season.
Firstgear Fargo Gloves. This model has been revised so I don't know if it is still as good, but they were cheap (under $60 I think), have been totally waterproof, and are a very good balance of comfort, warmth, and tactile feedback.
Honorable mentions would be my Sidi Adventure boots and Olympia Bushwacker jacket.