Regarding your points:

1) As I said in my piece, there's a huge difference between depicting something and endorsing something. The film in no way endorses Lester's lust for Angela. Yes, it is uncomfortable to watch but that is the point. I don't think this is a theme that has "aged" as it was, is, and will continue to be an issue, I daresay (unfortunately).

2) Well, I'm from the UK so can't really comment. A lot of American houses in films look unrealistically large to me, but it's never bothered me in terms of suspension of disbelief, regardless of the economic times.

3) This I suspect you may have a point about, but on the other hand, the film, whilst contemporary at the time, is now essentially set in 1999, so things were different. Again, I don't think that "dates" the film so much as provides a window into the past.