Any suggestions on alternate roles to look for? I'd worry that just because it's a software organization, it doesn't mean I wouldn't be filling their own version of cog in a cost-center.
So time spent using X is great, but just saying "I can learn" and giving an example of how you're able to learn is often enough. Then just look at X enough that you know the gist of it, have a small little sample project in your github account, and you'll be good enough that someone will hire you.
These people should focus on improving their credit, cutting expenses, and building up savings so that they can take the salary hit that will get their careers on a better track for the ~20 years until they're eligible for retirement.
Alternatively, these people can go in through a social backdoor. Befriend a powerful person at a company you'd like to work at and demonstrate why he needs you. If he has authority to set salaries, he will likely do everything possible to accommodate your higher-than-market salary, even if he can't get you 100% of the way there.
But beware: overpaying an employee is the best way for a company to trap him/her. Do everything possible to not become dependent on a rate you can't easily command somewhere else.