It would, provided that you are not dealing with lots of files.
If you are dealing with lots of files then you need to make sure
- there are no duplicate filenames
- you have an easy means of generating the index tags
I don't have a Kindle DX (though we did buy a Pocketbook Pro 902 for someone and that does seem to support a normal directory structure) but I believe that those outfits which sell packaged aero data like the European AIPs for the Kindle are processing the PDFs with some kind of automated script to add the Kindle tags to them, so they can be searched for.
If OTOH you have directory support then you don't need any of that. You just create directories for country / airport / whatever and then all you need is a decent file browser. That is the kind of thing which you get very nicely with Goodreader on the Ipad, and I imagine similar solutions for Android.
I think the Kindle DX is stupidly crippled but then I guess Amazon know their market
