i only had ONE guitar that barely cracked the 2K point.. my R7. TOTALLY worth it to me. otherwise, the bulk of my guitars have been in the 500-1K range. Had a really nice Esquire that was close to 2K, but sold it.
I guess I'm lucky or just patient. I've owned some incredible guitars, mostly made in the US and never gone over $1k. The most I've ever spent was $925 on a '65 ES335 12 string.
I'm cheap so i always try and get a deal or find stuff cheap so 2K was the most I ever spent, but luckily some old things I happened to buy long ago are worth more.
$5000 for a PRS Modern Eagle about three years ago. I sold it as I thought it was not worth it. In fact, to me, no guitar is worth it. I sold it for about $4850 and learned from my percieved mistake.
Now, I'm hard pressed to go over $3k for any instrument. I can have as much fun with an instrument for less money.
I have a Martin D-18 Authentic and a 000-18 Authentic, both of which I purchased in the $5K range. Both, though, involved major trades.
I think with acoustics, the quality improves significantly when you get above $2,500. With solid body electrics, I really like the $1,500 to $2,500 range. With both, you can get excellent, excellent guitars for much less than that.
I still think guitars are cheap in comparison to other instruments. A cellist will pay over $70K for his/her primary axe. I have vowed to always buy used cars instead of new cars and use the difference to justify my music purchases.
I bought my cello used for $1500 - it belonged to an orchestra player who had one too many lying around his house. I'm don't pretend that it sounds better than Yo Yo Ma's personal wood cello (he played a synthetic one too, for outdoor gigs), but you don't need $70k to get started. I only bring this up because I've seen some people here expressing interest in taking up cello as a secondary instrument. I do find the cheap student models that go for under $1000 to be thin-sounding, but you can find deals in the used market, and the $2000-$3000 new ones made in Asia and Eastern Europe are pretty decent
Most expensive guitar to date for me: Steinberger GM7TA from MusicYo.
I won't buy an expensive guitar again until I'm really ready for it. The main reason is I want a fairly flat radius (probably 16") and a D neck shape, among other things. Still haven't decided on other critical parameters like whether the neck ought to be compound radius with 16" as one extreme or just 16" all the way.
Only $420 CAD for me, for my MIM Strat, and a MIM Tele I used to have. I'm on a low budget because of circumstances, but even if I had the choice, I propably wouldn't go over $500-$600. It's a personal choice for me, since I don't gig, just play by myself so I don't want to spend too much cash on high-end guitars.
Most I've ever spent was 1300. Every guitar I have now was under 1k, and they sound just as good as anything else I've tried short of a few vintage holy grail guitars.