You’ve been getting some very good advice here. I particularly like the idea, I think it was @ProfFalkin’s to just get the entry level stack and learn for a while. It WILL serve you well for a long time.
But I wanted to give you come complimentary advice. First, I fully understand coming into the general audio hobby with little prior experience. Second, many of the things that people talk passionately about are rather subtle differences, and only become important when you have gained some time in the hobby. Third, companies market and throw all kinds of numbers and specific chips at you. Numbers don’t equate to musical enjoyment. Unless something is totally whacko.
What does matter is often not found in the numbers. All of the circuits and electronics that feed those chips are JUST as important as the chips themselves. A good chip fed by bad electronics is crap. A merely competent chip in a properly designed system may be stellar.
Another thing that matters is how you will use the equipment. I have a few DACs. I have a TEAC DAC with old Burr-Brown chips in my main stereo. It’s 10 years old, and plenty good enough for what it does. It has all the inputs and outputs I need in the main cabinet. That’s why it stays there.
When I want super-portable, I have Dragonfly (Black and Blue) DAC/AMPs. They’re tiny. I use them with my iPhone. Their output is limited, and while I thought they could properly drive a headphone amp, they’re really not well suited for that. (thank you @Torq). They are the best DACs I have for handling MQA. (Tidal masters). They happen to use ESS chips.
I mention these because it took me probably 3 f’kin YEARS to start to understand DACs. I did have some experience - in regular old fashioned hi-fi, not digital. I didn’t even know WHY I might want a DAC, let alone more than one. Perhaps I’m slow.
Now for the TWO DACs that I consider my main ones. The first I got is the iFi xDSD, which is a combination DAC and AMP. It uses Burr Browns. So what. I have a soft spot for Burr Brown because of the wonderful amplifier chips they made years ago. iFi happens to have an entry level DAC that competes with Schiit. I like both companies, not making a recommendation.
The reason I got the iFi xDSD is that I wanted a DAC and AMP in the same package, it’s small -ish, and it has a proper line-out mode so unlike the Dragonflies (Dragonflys?) it CAN drive a headphone amp. I use it both ways, as a combo unit and a DAC amp. It’s darn good. I was carting in all over the house, and on trips across the state, although it’s not as tiny as the Dragonfly.
Finally, I recently got a Schiit Bifrost 2. Lots of reasons. Yes, I’d heard a lot about its very good USB interface, and its fancy multibit chips. But the REAL reasons I got it were that it has exactly the right input and output for my main listening headphone station, AND it matches nice with my Schiit Lyr 3 amp. Aesthetics and practicality, not so much the chip. Yes, I can hear a difference between the Bifrost 2 and the xDSD in the same chain. But it is a very small difference.
So it’s use case, quality of build, battery life, ease of connection, overall sound. These are all more important than chip A or chip B. And it’s SOURCE, HEADPHONE, AMP, DAC, Connection in terms of importance to your sound. Source and Headphone are close to tied, and you can substitute Speaker for Headphone if you are listening to regular stereo.
In closing, I think it was @Resolve, who said that he could live with the Koss Porta-Pro headphones.(about $50). So could I. And probably a lot of the rest of us. For all that we appreciate the expensive stuff, I point to that because 95% of the general listening public, including people who buy Airpod Pros have no clue about things that really provide a quality listening experience. So you’re already on the path. Don’t agonize over marketing details. As I have said before, in this hobby, there are many kinds of goodness.
Best of luck and enjoyment with the choices you make.