I rode 8 years and 30,000 miles on a $300 hybrid. I probably would have ridden the $50 ancient 10 speed that I had before that, but it was far too small for me and I hurt after riding it. I think if the bike fit, I'd have made it work. Probably would have upgraded things. I did ride it to work maybe a dozen times total before giving up and buying a new bike.

I did also buy a lot of stuff to bolt onto the $300 bike, but little of it was necessary. My roads are pretty harsh and I did need to build a new rear wheel, I broke 12 spokes in 2 months. Apart from that though, most of the other buys were optional.

After 8 years of riding I finally gave up this year and bought a new bike. Now, 5 months later, I'm buying another new bike and retiring the old hybrid (the 2nd new bike is similar but much higher quality).