If you are stressed about the train tickets and knowing which pass will serve you best, consider consulting with a travel agent that can quickly sum up the passes and probably tell you which is best for your needs. You definitely should have a rough idea of what countries you want to cover if you want to buy a pass here in the states. There are a wide variety of passes for sure. Personally I want to do all my own research so I like Rick Steves information on how to pick a pass, he covers every consideration and provides you with a summary of many potential scenarios. (http://www.ricksteves.com/rail/home.htm)

Regarding how to dress, I am conflicted about the same thing but i always end up opting for comfort since that makes me a happy camper. I respect all people and always behave in a tolerant and kind manner, I always follow the golden rule ( do unto others...) and hope that this presents me in a favorable manner no matter how differently I dress. This is really a personal thing, if you are the kind of person that likes to blend in you will need to dress up since all Europeans seem to dress much more formal that us Americans. You will only be branded ugly American if you BEHAVE ( not dress) like one. Know yourself and follow you intuition.

The money thing is much less daunting than it seems--use your train travel time to ask questions of friendly travelers who will always share information. Travel second class to meet locals, bring a few pictures of your hometown and family and discover what an ice breaker sharing those pictures can be! Most people love to help.

Don't let frustration get you down, relax and let go of any notions. Winging it is a fabulous way to approach Europe as long as you bring an open mind and a gracious heart. I cannot think of a more adventurous way to go and i envy you doing this. I imagine that whatever unfolds for you will be perfect. Go for it!

All the best, Amelia in Los Angeles