I would echo using Monoprice for cables. Most people cannot hear any difference between a $1000 cable and a $10 cable, so why waste money on $100 for cables.
I would not get a Regen or a Wyrd unless you have specific issues with your DAC (note, I have both). Even then, get a used Regen for ~$100 or a used Wyrd for less -- but
only if you have issues.
For a DAC, any decent $250/300 DAC will be great. A used Bifrost. A new or used Mimby. Even a Modi is great. The Peachtree DAC-ITx is also very good, especially used for $200 or less. A CEntrace DACmini CX for $300 is also excellent. As are a dozen other DACs in this price range. The iDSD Micro or CEntrace DACMini CX might be a great starter system, and then get a better amp after you try it and really A/B test to see if you are getting value from a separate amp.
The Jodie is an excellent amp, but the iCan SE is as well, and has bass boost and 3D (both analog, not DSP). If you also want an integrated speaker amp, you must look elsewhere. Still, there are many amps in the <$500 price, but the Jodie represents and excellent value.
The headphones will represent your highest price single item, and will affect your decisions on all the other equipment (for the most part). Bottom line, if you are like most of the fools here (as am I
, you will always want something better/different. Make sure to try as many brands and headphones as you can. Go to meets and shows and stores. The difference between a $500 headphone and $1000 headphone is significant. The same price difference between DACs and amp will be very small for vast majority of people. The price difference in interconnect and headphone cables vs the value is insignificant. Cable upgrades are for people that have money during holes in their pockets are are looking for that last 1% better sound, even if they cannot tell the difference in an A/B test
Mostly they hear a difference and call it "better" because the cable costs more.