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Which cards have caused the most rules issues? I'm thinking probably either eye or teh annoying. Not to mention teh new annoying

I'll mention the Licids . I seem to recall Wizards R&D jokingly denying the existence of the Licids because of the rules issues they cause.

There are really a lot of different categories possible.

Some cards generate a lot of questions even though there shouldn't be anything confusing about them. Bond of Agony is a prime example of this. The in the mana cost works just like the in any other mana cost, but many people still ask questions about it, thinking they can just ignore that .

Some cards have historically caused rules problems but now work consistently, though the involved rules may be complicated. Humility is a good example of that. Thanks to layers, we can figure out the exact game state if we know what effects are involved and what their relative time stamps are. It just might take some effort and might be a bit unintuitive. Prior to layers, though, it was a real mess.

Some cards simply didn't work at all until they noticed it and issued errata. Purity , for example, couldn't work since abilities never deal damage ( Prodigal Pyromancer 's ability causes the creature to deal the damage). Void Maw and Uba Mask didn't work since they were making other things remove cards from the game; they weren't themselves removing anything. So those cards did have rules issues, but the rules issues have since been fixed with errata.

Some cards are trying to do something they shouldn't. This applies to older cards, mostly. In those cases, trying to give them sensible Oracle texts is impossible, since the underlying concepts are problematic. This often leads to rather convoluted Oracle texts and/or very unintuitive rulings. Some examples of this were already given in this thread. Raging River , Chains of Mephistopheles , Firestorm Phoenix , Imprison , Jandor's Ring , Ice Cauldron and Equinox could all fall into this category, in one way or another. We don't get a lot of questions about these, but it's mainly because they're old and not used a lot.

Indeed. I was checking my autocard links after I posted but missed that one. Sorry about the confusion.

The layer system managed to sort out most of the Humility questions. Even Humility plus two Opalescence is reasonably easy to analyse.

My current least favourites are Life and Limb or a combination of Titania's Song and Mycosynth Lattice . Urborg, Tomb of Yawgmoth in combination with subtype-setting effects are also not immediately intuitive.