As a hobbyist cyclist, I like having a decent bike simply because it’s more fun to cycle with less effort. Of course I could get an old crappy one to show off my skill and constitution, but that’s not the point for me. The point is to have some fun and while part of this fun is due to achieving goals, achieving a hard goal with a little help such as a good bike is still more fun than not achieving the hard goal, especially if it’s due to comparably-bad tech.
Whether your threshold for bad tech is now a really old bike or a not-newest bike is merely a quantitative difference and in the end subject to personal preferences.