I've been looking at the point to point prices on the DB website and it looks like the cheap fares are almost always unavailable. If I were to book all my trips with their lowest "available" price I would be spending close to $600. I was looking at the German Rail Pass option (six days in one month is 222 euros). Would a rail pass be a viable option or will I be told that all the rail pass seats are unavailable when I try to use it?
In Germany very few trains actually require reservations. If you do decide to get a reservation, there are just reservations, no distinction is made as to whether you have a railpass or a p-p ticket. Unless the train is already "reserved out", you can get a reservation at a ticket window or online, in advance, from Bahn.de, for €4 (2nd class).
The only time I have been on a completely occupied train (ICE), all seats were taken, but less than half were reserved. I could have reserved a seat when I bought my ticket, just a few minutes before boarding, and I would have had a seat.
Admittedly, I travel a little differently than most people, seeing more things in a small area and using regional trains, but in my last six trips to Germany, I spent less than half of a rail pass by using Länder passes and promotional fares. For instance, Frankfurt to Munich is a pretty big jump, but I found a lot of Dauer-Spezial fares for next month for €39 from Frankfurt to Munich, and €29 fares for April. If you're finding a railpass pays, you might be trying to go too far.