You're right. I'm kinda the same way. I look at various guitars and set ups and think 'Man, I would love to have this or that..." and then when I get home and start messing around with the guitars I have, I think, 'I LIKE the way this sounds". Sure, upgrades are inevitable but I think it should be more about your skills as a player as opposed to having the 'right' guitar as a status symbol.

There are a few things I DO want but not because I'm not satisified with the gear I have:

1) A Mexican strat (there is no way I'm paying close to $1000 for an American and frankly, I don't notice that much of a difference)

2) A little tube amp

3) A lower end Martin or Taylor (just because I love the mellow tone)

4) A resonator for slide work.

That's about it. But man, I know what you mean. I have a friend who buys nothing but less expensive, no-name guitars and such. He loves the varied tones he gets from them.