Electronic stores usually sell “refurbished” products also (meaning returned products in good condition). So, I see no harm in buying “refurbished” items and return them if you are not satisfied.

I also pay for a subscription (like Amazon Prime) to a store that allows 60 days returns and this gives me more confidence in trying and buying new things.

I tried using a few FiiO DAPs before (ones with Android and streaming), and they were slow and too much hassle for me. I got some portable DACs if I want to use wired headphones with my phone, but that’s it.

While this is very subjective, there is still enough agreement if you research a bit.

When I was starting with the hobby I got some well regarded headphones (from Beyerdynamic, Hifiman, Audeze, Sennheiser, Meze) and I wasn’t disappointed.

But nothing beats trying headphones for yourself. Also you can find some reviewers/sites with a good track record and similar opinions to help you decide.