I don't exactly how you came upon this itinerary or what your priorities are, but it appears that aside from Munich, Dresden and (maybe) Füssen, you wish to explore Germany's less interesting destinations. I would seriously reconsider the pace of travel AND your destinations. While there are some very charming old-world areas of Germany you might visit, about 90% of your plan takes you to major post-war-reconstructed urban centers; Triberg and Füssen are the exceptions but the tourist horde there will be heavier than normal (as you might guess, one or two other Oktoberfest folks might target Füssen as well) and there are better places.
Alps: If you'll be in the Black Forest (many fine towns here instead of Triberg!) who needs Füssen, which lies hours and hours away? You are already very close to the best alpine scenery in Switzerland. From Rottweil or even from Stuttgart you are only 3-4 hours by train from Luzern - and a DB savings fare there can be had for €19 each. Spend 2 nights there.
Dortmund-Frankfurt: You are bypassing the Rhine and Mosel Valleys? Wine festivals take place here every weekend in September, and you can see a real castle like BURG ELTZ (800+ years of history there) or Marksburg in Braubach. (Füssen's Neuschwanstein is a late 19th-century palace - not a castle at all.) OBERWESEL and other area villages like COCHEM and BACHARACH are full of attractive buildings with old town squares like Cochem's
Stuttgart: It's the area near Stuttgart that is generally more interesting. Visit Bad Wimpfen on the Neckar River to the north. Esslingen and Tübingen are very attractive cities. Bad Canstatt has it's own October VOLKSFEST - so who needs Oktoberfest?
Triberg: Just OK. You'd likely prefer other more scenic and interesting places:
Old walled town of GENGENBACH
Vogtsbauernhof
SCHILTACH
The BLACK FOREST RAILWAY cuts across the region from Offenburg to Donaueschingen through Gengenbach and several other nice villages. Train travel around the area is free with the KONUS card you get from hosts in the smaller towns.
I think you'd be wise to lop off the trip to Munich and southern Bavaria entirely this time because of the crowds and the costs. There's so much you're not seeing in Bavaria that it will be worth another trip - you'll be back. If you DO go, look into staying in Augsburg and doing a daytrip into Munich by train for O'fest. (Augsburg might also be a good base town for a daytrip to Harburg and to Nördlingen (very nice Romantic Road town.)
You may want to consider a GERMAN RAIL pass for this trip - an Interrail pass is another animal entirely.