Like you said, its subjective. I can argue from this point of perspective: Since Drogba is surrounded by players of the highest calibre, doesnt that make him getting more support which is of great quality? Lampard and Kalou for example, have been there supporting him. As seen as when Drogba is out, Chelsea still can get people to score, just highlights the support that the midfield and defend of Chelsea can provide. Being surrounded by top class players doesnt mean all the other players go for glory themselves, right? it just shows how much of great support Drogba get throughout the season, and i want to particularly highlight Lampard's contribution to Chelsea this season, IMHO is the greatest contributor, even ahead of Drogba.

In Rooney's case, we have a "sub-par" midfield, and an injury ravaged defence. They have enough to worry about with their own performance, what more to even support Rooney. yet Rooney can still get the most out of what he was provided, and turn them into results. I would also want to mention about the confidence of others he can boost within the team. Without him in the team, at time Man Utd looked clueless. Dunno what to do, dunno who to give the ball to. But with Rooney around, you can see the whole team being lifted spiritually. While it's Giggs and Ferdinand who wore the armband most of the times, Rooney is the "real" leader on the pitch on so many occasions. As for Rooney's award, the biggest he won is the PFA's Player of the year. This award is voted by PLAYERS in the BPL, Championship, League 1 etc etc. It is not controlled by English FA, or by any sports writers out there. So to get voted and acknowledged by your peers, it is something different than to be given the award becauce ENGLAND wants him to get it. Players from other clubs, for example Chelsea, can vote on their own best player, like Drogba. But the fact that Rooney won it, voted by his mates on the field, just highlights the contribution he did on field because after all, these voters are those who played against/with him and saw/felt his contribution, not some journalists who read match reports and statistics.

In a conclusion, for Drogba it is: 1 chance missed, more will come from the calibre-full support. For Rooney, it is: I have to make the most out of it, because it may be the 1 and only chance i've got left.

So, which is the bigger achievement here? Subjective right? 

No second guessing on who my vote goes to, but that being said, Drogba has been excellent this season