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David, thanks for your insight (you too Rand!). Any chance I could email / call you directly to discuss the idea? There are some implementation issues we'd need to address on our site to be able to incorporate a system like this.

Looks like you answered your own question. I would hesitate about changing existing URLs and make the update for future posts. If that's not possible, you must have 301 redirects working properly. Also, if your targeting Broadway Theater, you need to make sure that keyword exists on the page content and try to change the breadcrumb to read Broadway instead of New York.

I agree with the MadderPillar.  The third one tells you exactly what it's about immediately, which is why I think it is ideal.  Some SEOs report that there is a weighted system for Title tags, as well.  The first words in the title get more authority.  I've personally never experimented with this, but I tend to follow it to be on the safe side. I would also suggest adding in some additional blog posts about this topic: 5 Things You Didn't Know About Shakespeare 5 Reasons to Go To The Free Outdoor Shakespeare People love quick lists on Social Media, and 5 unique facts about Shakespeare would probably be worthy of a click from many people.

Assuming that you plan on posting them on your site as pdf files then they are spiderable to some extent. Google does spider and index some pdf's. I wouldn't advise this as a plan because pdf's do not generally rank well in most areas. The only category I can think of offhand where they do are irs forms. They would be much more likely to be thoroughly crawled, indexed and ranked if they are posted as actual webpages in html.