In terms of headphones, ofcourse no, you have to try a lot of them to know what you like. And you can put a lot on re-sale, it's not a concern. I never went into the hyper expensive stuff.

I did regret investing in a marantz pm7200 just to use it as a headphone amp, but I didn't know better at the time. Also got a tube headphone amp that I soon regretted but I was very lucky to sell it for a good price. Overall, I'd say this hobby hasn't costed me much.