Very good & sound advice. (Pardon the pun) 
Actually one of the largest aspects of investment in my own system is the Recording library. As @pk500 I think implied in the above, it provides an opportunity to redescover and savor your favorites with each step of the ladder. We always discover new music, but we only have so many cherished favorites. After we get exhausted of them, listening with an upgraded component starts the journey all over again.
Least this has been my experience.
This is so important, and something a lot of newcomers gloss over. You have to build a reference point, and the only way to do that is by listening to as much stuff as you can (with your own ears), whether it’s $50 IEMs or $6000 headphones. This hobby is a marathon, not a 100 yard dash, and those who choose to handle it differently will never fully experience and appreciate it. With that said, we should still do our best to assist and educate - we don’t want to scare anyone off because we mistreated them.
While I appreciate the vote of confidence in my SR1a review, you should pay due attention to the various caveats within. They are not for everyone, nor are they a headphone to dive into without proper auditioning.
You should also note that it was almost 3 years ago that I first got the SR1a, it’s been 2 years and 3 months since I wrote my review of them, and a LOT has changed since then.
Those changes include my entire headphone rig, excepting my tube amplifier, as well as my preferences and rankings for various things … especially in the face of the many new products that have emerged in that time.
As a result, you’ll be much better served by using multiple current reviews, from a mix of reviewers, and varying perspectives from posters on forums like this one, done in the context of what’s available today, to come up with an audition shortlist.
And in that vein, @Torq, where might we find your latest lists/rankings for various ‘‘things’’? I, for one, appreciate your opinions. TYVM 
One of the qualities some audiophiles like about the crack HPA is that very gooey overly warm syrupy sound. Personal experience through my network of friends most prefer a sound that is a little better defined, and the speedball helps in that regard. The crack should still have its overall sonic character but with better disciplined.
Even cheaper is the CCA CRA (and better in my personal opinion)
I don’t do that sort of thing anymore. Don’t remember the last time I did. Maybe somewhere in the CRBN thread, just for headphones, a few months back? But that’d be out of date now, too.
Prior to/other than that, it’d be a couple of years back and entirely out of date by now.
I’ll trust you on that. I haven’t heard them, but it seems everyone who has sings their praises. I’m fasting on further Chi-Fi purchases until 11.11 at the earliest. The CRA is at the top of my list for that day.
I’ll bite, can’t resist. From whence the specificity of the date for your, ahem, breakfast?
I promised my spouse, the CFO of our household, that I would not buy anything audio-related (except for ear pads and tips) until the next lonely boy shopping holiday.
Dusk is going to be the better option if you like rap. I’m a much bigger fan of the DUNU SA6 for its clarity and detail retrieval. Bass is good, and it suits a lot of music genres, but from many reviews I’ve read possibly not quite as big in quantity compared to Dusk. I have the OG Blessing 2. SA6 is just that next step up imo. Especially when you try something like an SR25 MKII which makes the difference clear as day.
Welcome @Earworm to the forum. I know a few people have pushed back on your idea of launching straight into an endgame setup, so I won’t bother doing that, although I do agree with them.
Instead, if this is really what you want to do, then we all want you to think about what you want to get out of your gear, so that you don’t inadvertently buy something that you don’t like.
Let us know what kind of music you like. When you listen, what do you value the most? Some people like a huge soundstage. Some want a piano to sound exactly like a piano in real life and if it doesn’t, then it doesn’t matter what other qualities the system has. Some want aggressive music to sound aggressive whereas others want it smoothed over a little. There’s no right or wrong here, but it’s important to know what you like. Take a look at this post I recently wrote on this topic, which had a link to a DAC comparison. All the DACs in that comparison are really good, but only one or two of them might be right for you depending on your preferences.
Also, what country/continent do you live in? This is important, because it may be cheaper to buy something from a local company, or you may get better support locally.
The more we know about your likes and dislikes, the more we can help. For instance, it’s great to know that you mostly listen to 16-bit 44.1khz music. I do too, and discovered that I liked the TT2 by itself but didn’t like the way the M-Scaler made the TT2 sound with 16-44 files, and I would have wasted a lot of money getting the TT2-M-Scaler combo.
The type of music you listen to is important too. If you predominantly listen to metal, people are probably going to steer you to something other than a RAAL, unless you’re going to have a subwoofer enhancing the bass.
The Crack’s goo depends in part on the headphones used. In my experience the HD-650/6XX results in extreme goo with the basic Crack. It’s a niche style with massive reverb, and fits my taste only for certain moods and some musical genres. Swapping the straight wall 6080 power tube to a shouldered/bottleneck 6AS7 results in more sonic structure too.
The basic Crack doesn’t get nearly as woo-woo-woo with any of my other headphones. I’d also not call it warmer than middling with anything, and is pretty bright with some tube combos.
As always “try for yourself and have fun.”
Building upon @PaisleyUnderground ’s comments, starting with a Sennheiser HD 600/HD650//HD560 or Hifiman Sundara are all real hifi headphones and cost effective entry point.
At that that point you’ll have a nice firm reference point that is more universally familiar with others in the community to have a discussion on what you would like to hear next.
With the Sennheiser‘s price point between $190 to $350 for a 230gram headphone is always great to have as a backup or when quality coupled with light weight is desired.
I just spent a week listening to a friends brand new $4000 Audeze LCD-4z. It sounded absolutely magnificent and really responded well to a little EQ. Switching back-and-forth I didn’t put the HD650’s back on and say “oh yuck“. They sound terrific and 50% the weight of the LCDs.
After listening to a $200 or $300 headphone, head to a CanJam event somewhere and try everything. Having a solid quality point of reference as a foundation really helps. If you look a few posts earlier, the team helped me navigate my next purchase as we had a common language using a known reference point for recommendations.
For my own path I just purchased a slightly used ZMF Aeolus.
Best of luck shopping.
Welcome to the ZMF family! I hope you have plenty of fun with your new headphones! For anything related to the Aeolus stock pads, it seems like more than 95% of their customers have not complained about the bass being too overwhelming. Aeolus suede pads get a lot of hype for making mids more 3 dimensional if you’re okay cutting down low end thump.
I have the original Blessing 2 and DUNU SA6. The SA6 is infinitely better for me when it comes to comfort. They’re so snug but not sinking way down into your ear like an overly large resin IEM from somewhere else. They’re awesome sounding out of the SR25. 
Plus it includes 3 different cable terminations.
Thanks Paisley for the detailed thought-out reply and questions along with everyone else who has chimed in; in particular with equipment / component chain suggestions.
Apologies, i thought i had mentioned in the original post. I listen to everything but rightly or wrongly, the motivation behind upgrading to even the noire/hip dac (with a view to upgrade further) was a lean towards classical and jazz. I’m probably not being precise, but the clarity, detail and separation of the instruments just blew me away vs. laptop connection unamped beats/airpods from CD. Not a metal head and not someone who needs eardrum rattling bass (have never felt the desire to utilize the extra bass feature on the hip-dac with the noires).
I am US-based. Not in a rush although i’d love to get the desktop DAC (which should run noires direct if they have any amplification) if only because having to regularly charge a hip dac is a bit of a nuisance (flimsy reason, i know).
I have a massive Jazz library. Almost anything you buy will trump Beats AirPods off a laptop.
If the baseline is the above, starting with $240 HD6XX headphones from DROP and with a quality DAC/Amp for under a $1K will sound impressive; and for many an end game solution. A quality used DAC & amp will save 30-50%. Resale from their will be close to what you paid. Makes swapping less painful.
This is an amazing DAC, analog volume w/remote, and good headphone amp. This box, laptop, decent USB cable, headphones are your done. The unit is $1900, but sell for half that gently used. I have 2 Stereophile A+ rated DAC’s and this Stellar Gain Cell is close in performance. There are lots of options. Steer clear of the Chi-fi stuff on Amazon as it looks nice but is performance challenged.
Standard recommendations here include the Sennheiser HD 800 or the upgraded HD 800 S. I own the 800 S and can confirm its stage is huge, while separation and localization are great. It preserves details and nuances, but its dynamics are weak relative to Focal products (e.g., Clear, Utopia). The 800 S responds well to amp changes, but with the wrong choice it’ll have thin bass (I sometimes use an equalizer to boost it) and little intensity. I and some others like how it performs with tube amps.
Is there any solid state amp that provides around 8 watts of power into 60ohm load?