Thanks for getting back with the names and screen shot that helps a bunch. I'm able to get the same result as you when I have an option group named the same or if the option has a single or double quote in it. To fix it I had to go into the db and get rid of the single and double quotes.
I have logged this as a bug so that it can be looked into further. In the mean time you should use the html entity version of these characters when adding products or options for the products:
use this for double quote:
use this for single quote
About the tracking charge is this an option that you have enabled in your USPS account? It is not something that I'm familiar with. If you know that there will be this charge regardless then it should be possible to just add $0.20 to each order to account for it.