I bought my bike well-used and am enjoying it at least as much as my last bike — which I bought new.
My bike is more than 10 years old and I got it for less than 20% of the price of a new one. In fact, the purchase price was probably equal to what the tax, prep and license would have been for a new one.
I’ve got no argument with the benefits of new, but there’s nothing on this bike that could break and cost me more than a fraction of what I’ve already saved. Even more importantly, it’s a model I really like and that fits my needs.
I think a big factor that will change whether new vs used is for you is how flexible you are on which bike you want. With new bikes, you have a fairly limited number of bike options, but whatever you see you can have (if you have the $$$). With used bikes, you have many more possible options, but the red-2003-with-optional-ABS that you lust for may never come up for sale in your community. Also, as you’re seeing, certain models keep their value and this reduces the amount you’ll save.
One trick I’ve often used with buying used vehicles is to read bike comparisons that pit your dream bike against similar rides. The top rated bike is often only marginally better than the 2nd and 3rd place ones. But this can result in lower resale for the also-rans. A few years later, the also-rans may be found for significantly less than the bike that beat them. And the real-world differences may be minor.
But one final word — unless you’re broke, don’t buy a bike you don’t love just because you can save some cash. You’ll have wandering eyes and end up wanting to dump in a few months.