The 58X is a solid starting point. Personally l, I’m really enjoying the 560s right now, but it is more analytical than the 58X. I think it’s on sale at drop for $150 currently.
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The Asgard 3 will not have any issues driving anything in your short list.
Hifi audio is a crazy hobby. I come from the home theater side of audio and headphones is probably the deepest rabbit hole behind vinyl/turntables (which I am dipping my toes in as well)
You are going about it properly by doing your homework. Your cans will have the most impact followed by the amp and then the DAC. I still have an entry level DAC (Topping D10) and will venture out with more research.
What is exciting is that budget gear has come a long way to the point that you can have a great hifi experience for peanuts compared to even 10 years ago.
You might try to pick up a couple of different flavors of budget IEMs to see what sound signature you prefer. The Tin T2s started me down the path to figuring out that I prefer neutral bright
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Thanks you for taking the time !
quick question. what do you think of the magni 3+.
and while I have no doubt the the Asgard 3 has more than enough power, does it deliver the smoothness? I read for example that the Heresy is too clear and detailed which is not what I am looking for. I am looking for the enjoyment, not the detailed 100% transparent studio sound. so what do you think ?
asgard 3 has a warm tuning. heresy is schiit’s answer to the thx fanboys. the magni 3+ is the mini me of the asgard 3.
zen dac + hd600’s is anything but bland. just saying 
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I’d argue the Heresy is better than most thx for less… it’s impressive for sure.
Magni 3+ or , liquid spark if you want enjoyment…
Could probably argue for the an Geshelli Archel 2 as well…
I still listen to my liquid spark… did today in fact with the 6xx
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I’ve had my HD660s for almost a month, and have never looked back. No regret, no buyer’s remorse, nothing. Just pure enjoyment of listening to music all day while working from home.
I will say that watching movies is kinda weird with them for some reason and I can’t figure it out yet. But all the music I’ve listened to has been a great experience paired with the jds labs atom stack.
The 1990 is an analytical headphone, the 650/6XX and Jubilee are not.