I am about to update a RoboHelp project that was created with version 5. I have version 7, and version 9 is the latest. These are the considerations that I can think of:
Would RoboHelp v9 help with any of this?
I think there are definitely benefits to upgrading BUT I don't think any version of Robohelp will help with your specific issues automatically.
1. Image maps - you might be able to get this to work, but I suspect you'll have to do the work in Word or Acrobat to implement it. I've never tried tried it myself. Or set up conditional tags for PrintOnly and OnlineOnly and define image maps for online and some other output - maybe image plus text links - for pdf.
2. Flash - to me, pdf is intended for print, so I can't see how flash would work. Maybe it's a fancy feature that you can implement within Acrobat, but again I suspect it would be post-generating to either Word or PDF.
3. I've always found it better to output RH to Word, run a macro to tidy up a few things (reapply a couple of styles, create headers and footers, make table rows not break across pages), then generate the pdf from word.
You need to ensure you've set up a Word template with the styles you need, then in the SSL you can map your RH styles to the styles in your Word template.
Additionally the upgrade will require some work on your part to deal with legacy issues from RH5 - do a search on numbering in the forums for details on these issues in RH8 - I believe the situation will be very similar for RH9. Plus Peter Grainge's site has more information as well: www.grainge.org
4. Sorry, I don't have any experience with RH7 + Captivate. Maybe someone else has experience with this combo.
Hope some of this helps.