1) Are there any "pilot wings" on the confed uniform?
Yes. In the original game they're on the left side of the chest, above the ribbons. In the FMV uniforms they're on the right side, below the name badge.
2) How many ribbons and for what did Blair get?
That's hard to say - he's probably earned dozens of them (you don't wear all your ribbons).
In the original Wing Commander he started out with two, for Academy Graduation and Flight School Graduation. Then he recieved ribbons for each fighter he was qualified to fly, each campaign he served in and for various numbers of kills and missions (ace, ace of aces, 5, 10 and 15 missions).
If you follow that logic through the other games and stories you add at least sixteen fighter qualification ribbons for the Broadsword, Crossbow, Epee, Ferret, Morningstar, Sabre, Arrow, Excalibur, Hellcat, Longbow, Thunderbolt, Dralthi II, original Rapier, Lance, Bearcat and Tigershark.
Campaign ribbons are a bit harder to guess. Off hand I can think of maybe ten: three Enigma Campaigns, Operation Backlash, Operation Thor's Hammer, the Firekka situation, the Deneb Campaign, Operation Red Three, the defense of Earth, the events of Wing Commander III. Of course, some of these individual operations may not warrant ribbons...
In the 'real' military you generally recieve a ribbon that represents any medal you've been given - so that would add a bunch more.