I don't mind installing Java as necessary as long as it works. I am not going to try Sierra until I hear that CS5 works properly with no glitches. Not the TM bit but saving out all my new work and photos, mail etc from ElCap to external storage and then copying all that back into the old Yosemite as it was before the upgrade. The process of reverting back to Yosemite via TimeMachine was painful. Then following forums etc I went deep into the differences between where bits of Java are stored in Yosemite vs ELCap, can't remember everything I tried but in the end gave up. I could work in it and save files etc but had the issues mentioned above.
When I tried to get CS5 working on ElCap I installed the recommended Java which gave me access to Illustrator CS5. You say you have access to Illustrator CS5 but is it working properly, not crashing on quit, saving your preferences, eyedropper not causing crash etc?
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