@Nick Got it. In your case it may just be choosing the lesser of the evils: i.e. no approach is going to work perfectly for you.
I find Markdown to be very easy and enjoyable to use (especially relative to Styled Text) but …:
- I find it easy to link to other pages or images. I realize you want the super-easy way supplied in Styled Text. But realistically I find finding/using the full URL approach very easy.
- image positioning or resizing: I never do this in Markdown except for when I want simple designations: 100% or 70% or the such width. Easy to implement with HTML via TextExpander (or similar)
- doing anything fancier with images would lead me to use another stack anyways (doesn’t matter if I’m using Markdown or styled text): two column stack, Pro Gallery stack, etc. So I don’t run into the same problem as you.
- smart quotes is a crazy lingering issue. It really should be fixed. That said, I don’t think of RW as a writing tool, but as a design tool. All my text is written in Scrivener (or iA Writer) then copy/paste. This avoids the smart quote issue. But I understand the pain others feel when they encounter this issue.
- I don’t use resources: I warehouse all my materials directly. So maybe this is a bigger pain-in-the-a##.
In my workflow I feel like I’m always fighting something when I don’t use Markdown! To be fair my websites tend to be text heavy (course websites) with a decent inclusion of videos, audio, and images.
Finally I definitely tweak CSS so all my headers, paragraph text, block quotes, etc. look just as I want them. But I would do this no matter using markdown or styled text. The “fiddling” with sizes, bold, etc. etc. in Styled Text on an individual level would drive me nuts.
… so in the end there may not be a perfect scenario for you. Is HTML, Markdown, or Styled Text the best compromise for your needs? I’ve chosen Markdown. Who knows, perhaps in a few years I’ll choose HTML. But styled text approach drives me crazy: the only (very small) advantage it has for me is the linking feature.