You must be truly dedicated to skate with pain for so long!
Most custom skate manufacturers provide a money back guarantee on fit, if you call soon enough. I don't know if Jackson currently does, or whether either of your prior two attempts were customs - but it is worth talking to them to see if they are willing to do anything. You could also talk to your current fitter to see whether he is willing to make good in any way. Those might be your first options, before modifying your boots, because modification might invalidate any such warranty. Given your prior problems, and the amount of money and pain you have put into this, it might be worthwhile asking each manufacturer whether they are willing to guarantee good fit, before ordering another pair. And in your place, I would go to the factory store, or to one of the travelling factory fitters the company sends.
For what it is worth, though this was years ago, Mike once told me that Harlick full customs were more customized than than Jackson full customs. He sold both brands, among others.
Incidentally, every custom skate maker has skaters who are most happy with them. No one skate maker seems to make everyone happy. I don't know why that is. E.g., some people on this board have been happy with Avanta (which inherited a lot of Klingbeil's bootmaking staff), who, if you go to the factory, can have their own staff podiatrist look at your feet. They often make casts of your feet. I don't know whether they merely take measurements from those casts, or they actually create new full custom lasts from that cast, but it at least sounds like a great way to go. (I also don't know whether they still have the custom last-making lathe Klingbeil sometimes used.) They are also willing to work from casts made by your local podiatrist.
I wonder if you could still call and/or email Mike and get suggestions on who to go to.
1. I have skated without the insoles before and I hated the way it felt/it didn't really relieve the pain, just delayed the onset a bit. But I'll definitely try again now that something has been done to them. (I had actually bought cheap insoles from Target to try this, but talked myself out of it since the pain hasn't changed at all.)
It sounds like you have already tried just about everything easy. It is quite possible that boot modification won't be enough.
But precisely what didn't work about taking out the insoles and skating sockless? Did it still pinch? If not, you maybe can reshape those cheap Target insoles, with tape, to get what you want, or cut new insoles out of foam, to fit the 3D shape of your feet.
If it still pinches, after the best Jackson can do, as well as removing or changing insoles and skating without socks, you could always try Agnes's destructive suggestion
http://icedoesntcare.blogspot.com/2013/08/surgical-intervention-on-figure-skating.htmlthough that would be scary to me, because it is non-reversible. At a guess, it would tremendously reduce the boot lifetime, because the cuts would continue to tear - but it seems to me that they already have a lifetime, for you, of near zero. Maybe you could put something over the slits that would hide the cuts. I'm not sure if anything could stop them from continuing to tear. Perhaps someone here who knows more about adhesives could suggest something.
Some Cabin John rink freestyle skaters told me they go to a skate tech who works at the Ashburn, VA rink. But they didn't know the tech's name. It might or might not be the same person who works at Fairfax - but bear in mind, you probably want the person in charge, not just someone who works at the shop. That's true at almost any shop.
I asked Mike once about a Chicago area skate tech, John Harmata, and he said he was top notch, and did the same types of things he did. But he is a long ways away
I think there is supposed to be a good skate tech near the University of Delaware, but am not sure, and didn't manage to find the name. Since that University has a
High Performance Figure Skating Center and frequently publishes articles on figure skating performance and medical issues, someone there might know.
Based on your pictures, I'm not certain, but it is possible that just tracing your feet, and/or getting foam foot impressions, won't be enough, because it is possible you have somewhat higher volume lower legs and upper feet than most skate companies assume, which is part of the reason you need a wider tongue. For that you need a top notch fitter - and preferably the factory store, as mentioned. I have a little of this problem - I don't need extra wide tongues, but need to center mine carefully, and to use laces longer than the boot maker provided.
BTW, for medical problems, I saw Mike refer people to a Baltimore area
Dr Paul Meissner and I think to a Delaware area DPM,
Dr. Jonathon P. Contompasis, both of whom have helped a lot of skaters. I didn't go to either, but I've met about a dozen local skaters who were misfit by the same skate tech I was, who were happier after seeing Dr. Meissner, and a lot of the other skate shops refer people to him too.
I wish I could give you a magic solution to your problems.