I've only started collecting Taskmaster comic appearances recently, so I can only recommend stuff that I know of (or have):
1 - Taskmaster 1 - 4 (Udon 2002) - without a doubt, the best mini he has and it's all about him and Udon's awesome alternate look
2 - Gail Simone's Deadpool run (Classics 67 - 69) and Agent X. I read somewhere that the next Deadpool Classic TBP - will have all these together - I'm waiting for that to come out so I can get them all in one go.
3 - Siren Infinity + Siren 1 - 3 (Malibu Comics 1995) Even as a just supporting character, his short appearances in the mini are all relevant and show a lot of him in the role of a "teacher"
4 - Taskmaster: Unthinkable (2011) - not a fan of the art, especially not happy with the story. In fact, I recommend you take it after reading the first 3 recommendations just so you have a good comparison perspective because this mini has inconsistencies and conflicts with his established lore. But my gripes aside, it still IS an important part of Taskmaster's bio, and a good thing to read moving forward.
5 - His appearances in Avengers: The Initiative (As suggested by TheReaper111). I agree with this 100% because again he's put in the spot of the mentor, but with a cruel villainy twist. He's got plenty of awesome moments in it leading up to Siege.
Keep in mind that with the exception of a few, Taskmaster (being a villain) is usually placed in a supporting or antagonistic role. Meaning most of the time, the focus is not on him. But he's usually a badass in most of the things he appears in.
Here's my collection, hope you find it useful.
https://www.facebook.com/photoreflex/media_set?set=a.679074875439381.1073741826.100000106241303&type=3
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