I put together a little squad and got slaughtered. I only took down 1 of my opponent's 3 X-wings. I learned from some of my mistakes, and would like to revisit the squad, but maybe with an adjustment.
"Howlrunner" (Swarm Tactics) 
"Dark Curse" 
"Night Beast" 
"Fel's Wrath" 
Academy Pilot 
Academy Pilot 
TOTAL 98 points
Considering my next game will be at game night with 2-3 consecutive games, I have thought about trading out the Academy Pilots for Obsidian Squadron Pilots to utilize those leftover points. The main reason this came to me was theme : I like it better when I'm flying with a named squadron instead of greenies. Not exactly a competitive reason, but I like to have a squad I can have fun with even if I lose. And since I have the points leftover, I figure, why not?
If I keep the Academy Pilots they will be able to ram the Rookies and Goldies (and other Academy Pilots). But even if I upgrade them, they will be able to jam up the flight path of higher-skilled pilots, and they'll be able to shoot the 2's and 1's before being shot. Of course, then I may lose intiative, but I don't see that as a huge problem for this squad with mostly middle-PS pilots, do you?
Let me know your thoughts. It's not urgent, but I've never asked for squad advice here, and I figured I'd have a go at it. But please stick to the topic of the thread. I already have about 6 completely different Imperial squads I could try, so I don't need any help there. Just want to know your thoughts on whether or not you'd upgrade the Academy Pilots to Obsidian Squadron Pilots in this case.
Depends on what you want to do. with skill 1 pilots it is not just about blocking others, it is also a guarantee that you WILL get your actions, so if you can get them into a very good position with focus, that actually translates to a very big difference that isn't too obvious at first glance. With skill 3, you will likely chew through other lower skilled pilots like rookie Xwings and gold Ywings and academy TIEs, alpha TIE/in etcetc so that isn't too bad either, and if your opponent doesnt have them then they are essentially the same as your academy pilots. in short, i tend to view obsidian TIEs as a sort of counter-pick, ie. you expect your opponent to field these lower ranked pilots and you want to get rid of them, so you upgrade your academy TIEs to obsidian TIEs.
otherwise yeah, i'd consider using the 2 upgrade points elsewhere, like maybe upgrade howlrunner's swarmtactics to elusiveness, or downgrade swarmtactics to determination and you have 3 left over points to turn night beast into a alpha TIE/in to go with your academy TIEs or something? I always find not much use in a single swarm tactic, unless it is paired with some specific uses like say garven or biggs. If you really do not have a use for those leftover points, I'd say upgrade them to obsidian if you could do a mass upgrade. no matter what, I will prioritize having them all at the exact same PS over having 1 or 2 obsidian TIEs and the rest all academy for eg. Since you could do that with your current list, I would say go for the obsidians.
tl;dr, Having all at the exact same PS level >> academy TIE + good upgrades for named pilots or TIE/in >> obsidian TIE en masse >> academy TIE en masse + leftover points