Your schedule is way to strict.
There is no way you will want to follow that schedule when you get there. What I would do if I were you is come up with a list of cities you really want to get to, and just make it a point to get there. Or have a general idea of the areas you want to travel in and let the wind take you along.
As for taking trains vs flying, in my experience, trains are a lot better if you are traveling between countries that border each other. I'm not sure how much European travel experience you have but the cheap carriers in Europe advertise as flying into Paris, or Oslo, or Frankfurt but in actuality they fly into a neighboring city that will be like 1.5 hours outside of the city so then you have to pay another 20 euros to be bussed from the outskirt city to the main city.
The eurail pass (
http://www.eurail.com/) Allows a lot of flexibility and works really well in my experience.