This may already have been suggested, but with Cakewalk, the program checks on
startup to see if it has any viable MIDI outputs.  If it doesn't, it will pop
up a dialog saying something like:

"There are no MIDI devices!"
[Set up devices] [Continue with no MIDI output]

...obviously, "set up devices" takes you to the MIDI device configuration
screen.  Might that be a useful approach?

Cakewalk works differently to Rosegarden in that the device config is a
config file in the program directory which is global.  Unlike Rosegarden
you don't have a per-song config, which is both good and bad.
On the bad side it's not very portable between installations unless you
bring the master.ins file with you.
On the good side, it's always there.  I hate to admit it, but I spent the
last 2-3 years painstakingly rebuilding the intricate MIDI setup (we're
talking 8 or more synthesizers) each time I import a MIDI file from SONAR.
It was only this Monday that I realised I could change the default setup.

Dunno if this is any use to anyone, just my 2p I suppose.

-- 
JP Morris - aka DOUG the Eagle (Dragon) -=UDIC=-  j...@it-he.org
Anti-walkthroughs for Deus Ex, Thief and Ultima   http://www.it-he.org
Project Future - A web comic                      http://project-future.org
The DMFA radio series project                     http://dmfa.it-he.org
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