I've supported England as long as I've been supporting Cov. 1985 or thereabouts. As I get older, I seem to care less and less about both, but that's probably a combination of me getting older and the way the modern game is now. I don't begrudge footballers getting paid massive amounts (why should they be paid any less than actors or entertainers?), but what it has done it destroy their priorities in the game. It's also destroyed the soul of football - it's now purely a global business and any sense of community is long gone. As Kuklinski points out, the players at the elite level are becoming very hard to like, the success would appear to go to their heads. But that isn't to say all modern footballers are wrong 'uns, there are still *some* great characters in the game. Jimmy Bullard for one, although even he put money ahead of his actual career.
For me, the 1990 World Cup was the highlight of supporting England. Is it nostalgia talking? Probably. But I idolised those players and Sir Bobby Robson, they seemed to care as much as we did. I cried like a loon when we lost to the Germans on penalties, I don't think I've ever cared more about a game in my life. Other than Wembley '87 and the Tottenham game to stay up in 1997 maybe.
If I had to choose, it would be Coventry every time. But I still support both, foolish as I am.