HA! I have SO missed keeping up with this group. :D
Jeremy's made macros so much easier to create (on the fly, even!) in TW5 that I was tempted to do just that — but then I remembered how I'd "created" styles when I first discovered TiddlyWiki Classic that, unknown to me, already had TW markup in place. I still find {{blockquote{some text}}} in tiddlers from before I knew about <<<. :P
Looking back, I'm not sure my comment "I can see where the markup doesn't have an elegant solution" makes much sense. What I was trying to convey was that the logic of TW5 markup doesn't have a blindingly obvious and easily agreed upon convention for wrapping an image in a link. TWC sort of did — or, at least, it seems like it did because I spent a lot of time with its markup over the years.
The more I tinker with TW5, the more I think Jeremy nailed it with his note about concatenation (e.g.,
[img[path/to/image.jpg]ext[http://www.url.com/]] or
[img[path/to/image.jpg]link[TiddlerTitle]]). That's consistent with the syntax in filters (and likely other places I'm just discovering) and streamlines the TW5 markup conventions a new user would have to learn. More complexity could be added by spelling out the full macro call and adding params, but it
does seem the lack of a basic syntax for image-linking is akin to MS Office coming without an out-of-the-box CTRL+F function. ;)