Railpass or point to point?

I have used both methods. Point to Point will save you money, however, I found I spent a lot of time in stations waiting to purchase tickets for our 'onward' journeys. Also, in Spain and Portugal the language barrier caused some difficulty.
I have purchased Rail Passes for our last two European trips and for me, this is the way to go.

I wouldn't bother with the pass. Buying tickets shouldn't be a problem - write down the train start and end stations, the number if you know it, and the times and just hand that to the ticket clerk. No need to say anything except hello and thanks.

Keep in mind that even with a rail pass you have to stand in line to buy the seat reservation unless you are riding a train that does not require a reservation.

In 1988 I went to Germany with a 16 consecutive day railpass for which I paid $160. I thought that was a good deal. So, when I came back in 2000, I paid for a 5 day German Rail pass (also around $160, as I remember). After the trip I added up the point-point fares for the trains I took, and I figured I just about broke even. I also noted that I had sometimes taken more expensive trains then I needed to. Since then I have always compared the cost of a rail pass to point-point tickets, accounting for advance purchase long distance and regional day passes, and I have never found a rail pass to come close to being the best deal. But, I always calculate the various options. If a rail pass is ever the best deal (which I doubt), I'll take it.

AP, I don't think you need to get 5 country Pass but a 3 country Pass. To get the most from the Pass, it has to be 8 to 10 days within a two month period. I am using a 10 day, three country Pass this summer too. What I would do is to buy a three country Pass (Germany, Austria and Cz Rep.) For the other places buy point to point tickets. If you're doing only day trains, crossing between Austria and Hungary, or Austria and Cz, or Ger and Austria, or Hungary and Cz, you won't need to reserve, just hop on with the Pass. Be sure to check that a particular route you're does not go through the Slovak Rep. To make the Pass work, don't take night trains where you have to have a couchette or a sleeper, (those are extra charges that cut in on your Pass savings), just sleep upright in a compartment. Take the ICE or IC trains when there's a choice and esp. on long rides. You can get the entire cost of the Pass converted to Euro, divide that by ten.

Germany has some of the best advance purchase and regional day tickets anywhere. I seriously doubt that you can make a rail pass pay in Germany. For connections entirely in Germany, there is the Sparpreis fare, from anywhere in Germany to anywhere in Germany, as long as one leg is by express train (ICE/IC/EC), starting at €29 pP. For connections going outside Germany, the Europa-Spezial fares start at €39 pP. There are also day passes, primarily the Länder-Tickets, for unlimited travel for 1-5 people all day on regional train within a German state for around €30±.

The longer your segments the better the pass vs individual tix. A trip I took Luxemb to Vienna to Luzern was perfect for the pass (long segments). My trip Amster to Koeln to Brussels & back to Amster was much cheaper buying individual 40EU tix. They were short segments, and I would need a 4 day pass. Im on my way to Spain & Portugal. Buying a 3day pass. Segment 1-night train Madrid to Lisbon. (Flying Lisbon to Barcelona) Segment 2 Barc to Valencia. Segment 3 Valencia to Madrid then to Toledo. $295.00 1st class pass will save me money. Each leg is more than $100.00. I will still have to pay a seat reservation, but I will be in first class(not a huge deal, sometimes the cattle car more fun)
When buying a ticket at the sta. you save $ buy using the ticket machine if you can manage it. Avoid waiting in line.