One of the reasons you get such apparently contradictory information from people trying to help is that “it depends” is almost always the answer. There are thousands of different headphones, streamers, DACs (many embedded with an amp), amps. Each persons experiences are different and usually confined to only a small number of components. Hence, someone might conclude that an amp is not required. However, one thing you can be sure of is that the best sound will be achieved by upgrading your headphones, streamer, DAC, and headphones. Personal taste will influence the final ”best choices“.
As far as learning and specs. I recommend reading Stereophile and The Absolute Sound. don’t dismiss reading about the flagship models. Not because you are going to buy them, but a company that can make a world class piece of equipment is going to use the same designs and techniques and materials to produce their inexpensive ones. Also, companies have ”house sounds”... really dynamic, or natural, detailed... etc. You will learn the vocabulary to describe the differences in sound and figure out what you want. I started out desirous of bass slam... along the way got it... but lost detail, balance and midrange. Highly detailed can really easily end up really fatiguing... high frequence noice... you better have really good upstream equipment.
i am lucky enough to have equipment that brings out the best in about any headphones. My Sennheiser HD 800s made their biggest improvement when I put the muscle of my high current ($4,000+ amp) behind it... but without the expremely high end Streamer and DAC that change would not have been so profound. The smallest incremental difference when I added my current amp was was my very efficient Focal Utopia.The Focal Utopia and Sennheiser HD800s now sound very very similar. I found that high impedance headphones are the hardest to get the most out of. Not that they may not sound good, but they require lots of power to be their best. But power without Finesse can lead to noice... or a cheap streamer / DAC can lead to noice.