i havent read the whole thread so apologies if someone has addressed this already, but i have often had trouble on various rims, including HED jet 6s and zipp 303. I get it, not everyone has space for a compressor, but man they make them so cheap and small these days and they are so handy for sooooo many other things, that i highly highly suggest getting one.
I have found that when i am having trouble normally, even with a compressor, i take out the valve core, put on an attachment that used more for just blowing air try to seal that as much you can against the now open valve stem and that has done the trick every time! just make sure to put your thumb over the valve once the bead sits in so you dont lose air rapidly and the bead pulls away. let the air out slowly or put the valve core back in quickly.
compressor are so much quieter and cheaper than they used to be. keep an eye at lowes or depot and you can find great deals. you dont need a big one. 1.5 gallon will be just fine. and they are so handy for kids bikes, car tires, blowing stuff out etc..... or go to Harbor Freight and pay half of that price but it might only last half as long and will probably be 2x as loud, but it will work!
https://www.lowes.com/...it-Ensemble/50129862 something like that works great for when you have the core removed. there are tons of stuff like that out there
https://www.lowes.com/...nflator-Gun/50126453 - then i bought this, cut off the hose and attached something like the following..
https://www.universalcycles.com/...yEAYYBSABEgJkO_D_BwE - then you have an awesome trigger pull set up with dual heads for shrader and presta and a semi accurate gauge. sure Sagan isnt trusting that gauge for riding cobbles at Roubaix, but for most of us, its plenty close.
Probably a little more than most want to spend but I am telling you, once you have this set up, you will find it so nice. sure i still use my regular pump alot of the time for my bikes .but if am airing up all my tires, or all the family bikes, grab the compressor and its done in a fraction of the time. and with the added tubeless benefit to me it was a no brainer.