Just a few suggestions as I don't have the time right now to do a deeper look at the problem:
Node.JS can serve up images, video, or anything else you might want. Whether TiddlyWiki itself though is coded for that, I'm not sure. Normally one simply assigns a route using Express.JS middleware to serve up static files. So there is a way to do this, I have done so on many websites, I just don't have the time at the moment to dig deeper into how/if TiddlyWiki itself is coded for this, but it is possible with Node.JS.
Regarding your links to your PDF files, I used to make this same mistake too. You need to use relative external links instead. The link format is a little different from what you may have been doing, but it saves you a lot on typing too.
I used to load PDFs into a browser tab and copy the URL into TiddlyWiki before I realized relative external links were available.
So if you have a subdirectory below where your TiddlyWikis are like:
And you have a book located in there like so:
./TWDataFiles/PDFs/Instant TiddlyWiki Development.pdf
Then you can link to it like so:
[ext[Instant TiddlyWiki Development|TWDataFiles/PDFs/Instant TiddlyWiki Development.pdf]]
Notice that you need to not use the conventional
[[title|link]] but instead use
[ext[title|link]] instead.
Good luck,
-Doug