It's pretty difficult to realize, but I have seen two ways to pull off remote work:

- Do work with a client locally for a while and earn their TRUST. Multiple contract renewals are a sign they really like you and need you and are likely to accept a remote working arrangement.

- Become a senior SWE and acquire enough skill and "brand" that you will be desired by the larger companies which make exceptions for this type of thing. I've many people, almost always in management roles, pull this quite well for a number of years. All the largest software companies have some remote managers and developers (Microsoft, Autodesk, even Google), even if at first contact they'll tell you they don't do that. Usually, those who get those exceptions are senior and their skill is in high demand (they're "experts" at something, or they're great managers).

I've never seen anybody get well-paid remote work in different circumstances (though that's not saying it's impossible).

When I first wrote Beancount (http://furius.ca/beancount) I wanted to reconstruct up to 7 years of history for some of my accounts. I ended up using PDF statements where I could get them, and entering some of the missing statements manually. If you have PDFs, cut-n-pasting into Emacs and massaging the entries to fit Ledger/Beancount's input syntax manually is possible (though a bit time-consuming). I created macros to help the task, it wasn't crazy.

If you use a double-entry accounting system like this, it'll save you so much hassle that you won't have to remember to reconcile: you'll just *want* to reconcile more often than you actually need to. It's really cool to know where the pennies are going.