Trials and tribulations of planning a major trek, emotional worries and doubts

I've been planning this summer trip to France and Spain for what feels like forever now - I started around Thanksgiving. Figuring out the European Rail system is difficult, to say the least, as raileurope.com doesn't have all possible routes available online. I've spent pretty much the entirety of this weekend (among many previous hours online as well) researching how to get to all the places I want to see in the time frame I have, and I've yet to feel reassured that I have the schedule solidly figured out. Part of the issue is the fact that I'm trying to do this a few months too early, as raileurope doesn't show most schedules previous to 60 days in advance (this makes the planner in me very nervous). The only problem with that is the fact that I'll be traveling during high season. This means that there is a high probability that if I don't reserve tickets as soon as possible, I may not have a seat. Oh, they'll still issue me a ticket on the train, I just won't be able to sit down! Highly concerning, considering the fact that most of the trips are over 5 hours! I am also trying to take advantage of as many night trains as possible, as they save me on hostel/hotel costs, plus get me to where I'm going early in the morning. No wasted hours! :)
Another perplexity is the difference between passes and point-to-point tickets. At first, it seemed a pass (the France-Spain pass in particular) seemed the way to go. Then I learned that even after buying the pass, I'd still have to pay for reservations on almost every train! After all is said and done, it seems like buying point-to-point tickets are the cheaper option, as the reservation price is included up front. Come the end of April, I'll be calling their help line and having a professional tell me the best (cheapest) option.
All this being said, I think I have a detailed-yet-tentative schedule figured out.

Some things I'm excited about:

• I'll be arriving in Santiago (provided I do it all in time. . .) on the day of their huge yearly party, Festival de Santiago. 2010 is a holy year (their saints' day (Santiago (St. James)) falls on a Sunday), so it should be super-charged with Galician parades, rituals, singing, fireworks. Downside: since it's a holy year, officials are estimating there will be twice the number of pilgrims on the Camino. Could prove problematic when finding hostels. Upside: twice the chance to meet new friends along the way!
  
• Getting to see Heaven Shall Burn in concert! They've been one of my favorite bands for the past 4-5 years, but since they're German they usually only tour Germany/Austria. They are actually going to be playing in a music fest in Viveiro, Spain (thus the reason for traveling back up to Ferrol) a few days after my walk! Can't wait for that. Very serendipitous.
  
• Visiting the town of Rocamadour. Look it up. I also really want to get to La Roque-Gageac, which is about 50 km away from Rocamadour, but there's a definite lack of public transportation in that area. At this point it doesn't look like I'm going to make it. :(

I'm sitting here now wondering if I'll actually be able to do it - get by alone in two foreign countries for 6 weeks without a solid understanding of either language with only a backpack, relying heavily on my own two feet. It's scary, exhilarating, nerve wracking, and mind consuming. There's a reason I need to do this, but I'm not exactly sure what that reason is. What if I don't find whatever answer(s) I'm looking for? What if I don't even figure out the question? Or perhaps even worse, what if I DO and don't like what the answer is, don't want to come back, or don't know how to get to the place in which the answer lies?