Latest RStudio on macOS Sierra here, I have that setting and have been using it for quite some time now, so I'm confident it is there, and it works.
Maybe try a different RStudio version (preview or dailies), or try changing your screen resolution, as window sizing seems to be an issue.
Annoyingly that options window can't be resized in general AFAICT, so that's not specific to your issue (even though mildly infuriating).
Your hardware UUID is also probably less important than your macOS version, so I can only give you general "make sure all your stuff is up to date"-advice, sorry 