Attachments are a new feature and I already have found that some type of special handling is needed. Some way for the author to specify a tiddler is to be stored as an attachment regardless of size or type; or specify the tiddler is not to be an attachment.
A checkbox on import should be able to handle that. A default can be automated, but the author is really the one to make the decision. For large media files indicate that due to size it will be saved as an attachment. The attachment checkbox would only be available on the MWS edition (or editions that use MWS).
A similar scenario is how images are handled by server edition. If I wish the image to be in the wiki (which is usually based on if I am going to distribute the wiki as a single file) I drop the image and import it - and the image is in the wiki. If the wiki is going to always be a Node.js wiki, I place the image in the ‘files’ sub-directory and use _canonical_uri. The important thing being - it is my choice.
Attachments should have their own field. _canonical_uri can exist anywhere and the author enters them, messes with them; exist on your machine, on the web, they can change if moved to a different host, etc. _attachment only exists on MWS, the uri is generated by and uniquely handled by MWS, they are special. For example, the author would almost never specify the uri. _attachment should for the most part be totally automatic. Best advise to an author would be to leave it alone - the only thing you can do is break it.
Attachments are a new and substantial addition to TiddlyWiki. The SQLite database has definite advantages but for the most part is transparent - is another tiddler store. But the attachments will be the unsung heroes of the MWS release (well, unless you got a song about them - if so, put it in an attachment). Would not be surprised to see attachments added as a ‘server’ edition feature at some point.
Now is the time to give some thought on how and where to integrate attachments into the TiddlyWiki Architecture; before the release.
Just thinking out loud.