I started out playing a Hammond organ and I was learning computer programming more or less simultaneously. I also work with computers and networks on the job, so moving to a keyboard was not a big jump for me, but I don't come close to using all the features of my keyboard. I haven't yet merged computer with keyboard. Still saving my money for a pc. I am looking forward to connecting them together. The o/s on my PSR550 (probably most keyboards)is weak compared to what I could do with a computer running XGworks. I would also like to buy Native Instruments B4 to get a good quality Hammond sound. From members comments here, NI B4 is of a higher quality then on the PSR2100, so connecting to a computer would be a better upgrade then going to a PSR2100. Not sure about expression pedal though. Uncle Dave, an expression pedal is more than just volume.
Starkeeper
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I play Roland EM20 and Yamaha PSR550