I have several comments that I hope you find helpful: Maybe this is a great opportunity to buy a Mac. I am a long-time PC user, but have been using the MacBook Air for over a year now. It is the best computer I have ever used. Moving to the Mac would allow you to: Import blocks of files to a specific Notebook with specific Tags Set the Note Creation Date to the file Creation Date Both of these require a 3rd party AppleScript (free) [*]I agree that it is worth some time/effort to design your organization approach, but don't worry to much about it. It's not like pouring concrete -- you can always change your organization later in EN [*]If you are used to a fairly structured folder, sub-folder organization, you will likely not be satisfied with putting all of your Notes/Files into one or two Notebooks with no tags While Search will find the Notes with the words of interest, it will also find Notes that have the same word(s), but not what you are looking for Judicial use of Tags will greatly aid in searching for, and returning, only the Notes of interest. This is particularly the case if the words you want to search for are common words likely to be in many Notes of different subjects. [*]Start out Slow Import a small block of files using whatever organizational scheme you select. Try searching for subsets and evaluate the results. Adjust your scheme/tags/notebooks as required. One advantage of EN Win is the Assign Tags feature: CTRL+ALT+T You could search/filter/select a block of Notes, and then in one easy Window assign/reassign/remove one or more tags to the entire block of Notes Good luck.