Well, it should work fine. But I encountered missing content problem when I upgraded from 9.5 to 10. I personally suggest doing completely clean install. I only spent 6 hours working it out…
Yes they co-exist! But be warned that 10 will mess up your preferences and other settings for 9.5, unless you copy or rename or copy and save the folder under User-AppData-Roaming-Steinberg-Cubase 9.5. Then you can name it back to original or copy the saved version back into 9.5.
If a clean install means uninstalling 9.5, then the option to going back to it on projects not working right on 10 or because you got fed up with new things on 10 and want to give it more time to learn will be lost. Usually new upgrades come with new or old bugs and some get sorted out with time.