Would a Dynamic IP address be safer than a static? The reason being that a Dynamic IP is different everytime thereby making it difficult for hackers to target you? My ISP offers a "security" upgrade for $5 more a month, I’m assuming that this is a Dynamic IP address offering?

Actually, most ISP’s charge extra for a static IP address. They do this because people like to run web servers from their IP and it makes it more difficult for them if it’s dynamic – and – by using dynamic, you can serve more users.
When you are given a dynamic IP address, you are give an address that has a TTL – Time to live. So, if your TTL is set to 12 hours and you don’t use your computer for 13 hours, you’ll be given a new IP address; but, if you use the computer withing the 12 hour period, then the IP stays the same. Many people run with the dynamic (low cost) package and set something generate traffic every few hours (doesn’t have to be a lot of traffic, just something) so that their IP stays the same – these people are also hosting a website or file sharing service, etc.
I’m not sure what the security upgrade is, but you’ll want to ask for details before moving forward.
Does a dynamic IP provide more security? You might say yes (lightly) and here is why: If you are nor running a website or hosting anything, and if a hacker had your IP, changing it would make it very hard for them to find you. Now, if you go and send the hacker an email, then he could look at the headers and see your new IP – or if you visit a forum under the same username as your old ip and it’s posted for all to see, then it wouldn’t do you much good.
So – yes, but consider it a step towards security and a very light one at that
Best regards,
Jim.
If you’re a user, dynamic is better.
If you’re operating a server, static is better.