Originally Posted by RobbieTunes

You're right, it's a relative question.
You kind of have to eliminate the real steals (mint Pinrello Montello for $800) and the ripoffs (87 Lemans RS, butchered, for $275 delivered-eBay).
You also have to consider that some collectors only want bikes that happen to cost more. I understand that, completely.

For me, though, it's "at what level of spending does any more money really stop having an effect on my riding?" For me, it's a grand.

I may be able to outride a $1000 entry-level bike, but I sure can't outride any build I've done for $1000, ...
...and I see darn few used bikes over $1000 that would significantly improve my riding ability based on their components and frame alone, compared to those available at or below $1000.

I'm probably as fast on a $1000 used/built bike as I am on anything more expensive.
I'm probably as comfortable on a $1000 used/built bike as I am on anything more expensive.
I'm probably as good looking on a $1000 used/built bike as I am on anything more expensive, because face it, bikes can't produce miracles.

I can't see anything out there over $1000 that improves anything but my ego, and maybe not that, because my friends would give me a pretty hard time, and my wife, well....let's say I'd suffer.

$500 to $1000, there's room for improvement.
The vast majority of my bikes are $500 and below, well below, but you can get some real nice stuff between $500 and $1000, so I voted $1000.

I'd have voted for $500, but the few bikes I have that go above that, well, they are pretty darn nice.

I see riders, especially triathletes, buying speed, or they think they are. Once you go aero, though, you still have to turn the cranks.
Good conditioning costs less in terms of money and works better. If I was gonna spend over $1000 to get speed, I'd try EPO.