A PDF file with embedded fonts is not affected by Typekit or its absence.
The interactive elements are much more unreliable than the fonts, disappearing or breaking in most browsers and on mobile apps.
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All the Typekit fonts are properly embedded in the PDF file.
It seems the exported PDF is fine, but my InDesign saved copy is all sorts of distorted and ugly dude to the entire font flow being disrupted every time I open the program and need to re-sync as it takes 10-20 minutes to 'find' the font.
Because you are opening an InDesign document that uses TypeKit fonts, it will need to sync those fonts if it is not already present.
Typically for distribution of InDesign documents, you would “package” such documents into a directory structure that copies linked content and fonts. The only difference with the Typekit fonts is that such fonts are not included in the package. But since whoever is going to do those further edits and/or PDF export also needs the CC version of InDesign, they will also have access to the same Typekit fonts that you do via the Creative Cloud software. There is no need to package the fonts from them. If they have older CS versions of InDesign, they will not be able to open your CC version InDesign document anyway.
My concern, based on my own experience, is whether or not the end user needs TypeKit to see my document properly.
No the user should not have Typekit to see your PDF file.
The other question I have is, once this is published - assuming the answer to the first question is satisfactory, do I need to maintain that font forever as a synced font to have it continue to exist inside the PDF?
No you can choose to not maintain that font forever to have it continue to exist inside PDF.
What experience would that be?
Every time I open InDesign, it takes forever to sync the fonts. I think it's an InDesign issues because my synced TypeKit fonts show up in other Adobe apps and are showing in my cc app. I have this problem similarly with the mobile apps where they constantly can't connect to cc. They tell me the feature I'm trying to use is for cc subscribers and direct me to their sales page. It's less of a burden because... well the adobe mobile apps are pretty sad and don't have a ton of utilization regardless - outside of Capture and Comp. You can see my screenshot of the issue at Shared album - Eric Williams - Google Photos
By the way... I've really been enjoying your content, super helpful!
I thought maybe at first, but since every other application seems to have no issues syncing (it's even in Microsoft Word) including photoshop, illustrator, cc, etc. - I think it's pretty specific to InDesign, or am I missing something?