Thanks for sharing your blog post, timfg. I'm in the process of doing this myself, and some of your ideas on client-side security were very helpful. I too have decided to go back retroactively through my old files, and thus I am currently spending 1-2 hours per night after the kiddo goes to bed feeding the scanning beast. :-) I have a strong motivation to avoid procrastinating - I'm moving in 5 weeks and I am determined to not lug all of this paper to yet another house. I find the process cathartic, as I've gotten to the point where I can sit there and feed in the documents and mostly keep my brain free to think about other things. One strategy that's sped up the process for historical stuff is that I tend to create larger PDFs which combine multiple documents of a similar theme, instead of scanning each of those individually. For instance, an entire course's worth of graduate school notes go into one PDF. All of the documents relating to a car I no longer own go into one PDF. The search is good enough that I can find what I need without too much hassle. For current stuff (e.g. my current car maintenance records), I'll be scanning them individually as they're generated, but I couldn't see any strong reason to do my backlog of files one document at a time. As long as I kept the PDFs reasonably small (I try to limit a single PDF to 100 pages or so), this approach seems to work well. Since part of my workflow is to rename the notes before they are uploaded into Evernote, this means a lot less stopping to type and a lot faster processing of the retroactive historical load of paperwork. Thanks again for sharing your experience!