As much advance planning as you can do will help you to be prepared and feel comfortable, even though you are leaving some decisions flexible. I would start with Rick's guidebooks, such as the travel skills book Europe Through the Back Door or articles excerpted from that at http://www.ricksteves.com/travel-tips. Then, get into destination details with the single-country books for each region of your focus. This gives you a more compact, one-stop starting place than searching the entire internet. Hostels are easy to find through hostel search engines, as well as Rick's books will recommend those he finds most useful, as will other guidebook brands like Lonely Planet.
If you are looking for a travel partner, there is a forum page for that, but you should not hesitate to travel solo. In hostels, you very likely will meet people with whom you can team up for a day's sightseeing, a dinner, or the next train ride.
Rick's traditional advice has usually included cutting the furthest, outlying points from the early drafts of your itinerary, which has often meant cutting Greece. Of course, Greece is not made closer by flying, such as from Rome to Athens, instead of taking an overnight ferry from Ancona or Bari to Patras.