Is there a service or GUI tool which, if it magically existed and understood all of these steps and so was only limited by the underlying cryptography involved, would noticeably mitigate or even dissipate your "dread"?
There's https://fastlane.tools, but I haven't looked into it a ton. It seems to require a big investment to get things rolling, but probably solves a lot of these problems after that. I'll have to revisit it at some point...
I am more trying to ask the question "what is the minimal modification to your current, depressing workflow that would have made your life easier: what is the magic artifact weapon you wish you had in your arsenal to cut through your pain points (or even just, what is your single largest obstacle in the middle of the battle, when boiled down to a single moment where a deux ex machina would have been useful)", as opposed to "would you be willing to opt into a totally different lifestyle of peace and love, it only requires that you disavow all of your current earthly possessions and relationships".