Ron,
Don't know if you have worked CW with the 590 already and you just have
a paddle problem, but have you turned on the break-in function? It's
the same as the VOX button for SSB, third button down from the upper
left corner of the radio. If this isn't turned on, you just get side
tone and no TX, either with paddle or straight key.
As for keyboard CW, most logging programs offer this, with the addition
of some hardware. What logger are you using?
73, Steve KW3A