I want to shorten some URLs, will a Re-written URL count as duplicate content?

I want to shorten some URLs, will a Re-written URL count as duplicate content?

Situation:

The corporation I am working for is undergoing a rebrand effort soon, which means our domain name is changing, and so we have a lot of SEO / Redirection issues to look out for.

My manager wanted to know if we could take the rebranding opportunity to rename/url-rewrite/redirect our older, non-WordPress sections, which were not given easily remembered urls.

Example:

We have URLs for our amenities which might look something like...

domainname.com/visiting/amenities/food_drink/starbucks

Though it is a "friendly-url", it is not as concise as domainname.com/starbucks. From my knowledge of SEO and URL Rewrite rules, I see the following solutions

1) If I set up a URL rewrite rule in IIS, I can get domainname.com/starbucks to rewrite as the actual path, but then both URLs are accessible via browser.

Would Google count these URLs as duplicate content, and knock my ranking down?

2) I could set up a 301 redirect if domainname.com/starbucks is detected. The downside to this is that the concise URL does not remain, so it's not as "pretty". The upside is that Google won't detect duplicate content, and the current indexing of the original URL will not be affected.

3) I could actually move the web content to /starbucks, and have the original /visiting/amenities/food_drink/starbucks perform a 301 redirect to /starbucks. This would keep the concise URL, and not count as duplicate content. Best of both worlds. The downside would be that this option would require the most work and testing since we might have absolute links to fix.

Do these three options sound about right? Am I forgetting/leaving out anything here as far as solutions go?