So, upon thinking about classic servers and how they will deal with the eventual "Lack of content" boredom that will eventually settle in with the Naxx raiders - it got me thinking of two things: 1) Blizzard's new love of turning everything into an E-Sport, and 2) Diablo III's Seasons Journeys.
Basically, I'm starting to convince myself that Blizzard may actually implement some sort of repeating "Season's Journey" into Classic servers to keep players a) Competing with eachother on leaderboards and b) to keep recycling the same content with the minimal work needed for "rewards" to keep Classic players appeased.
(EDIT: For those unfamiliar with D3's Season's Journey model. Every few months they announce a "Season" where you create a new character from scratch and meet XYZ number of goals in the given time. The more goals you hit within the timeframe - the more permanent rewards you obtain.)
Of course, just like in D3, the rewards should be purely cosmetic. Things like Frame portraits, special pets (especially if you can port them over to your main account! Cross-mode play promotion! ;P), or titles (if they choose to include the title concept at all since I don't remember titles being a thing in Vanilla outside the old-school PVP honor system). As long as they're cosmetic, it shouldn't interfere with the "Classic" experience. This is why I choose not to include any idea of "transmog" gear as a reward as a) Vanilla obviously didn't have Transmog and b) Because half the fun of endgame Vanilla was seeing what gear others got on. :P
They could implement it in two ways. either a) the simple method: a "Seasonal Classic Server" that resets every season, or b) the complicated version and have you be able to roll seasonal characters on classic characters, but they have restrictions on them like "You can only group up with other seasonal players" and the like...
What say you all?