i know the feeling man. I have always been a draw traditionally guy and for finished illustrations i may never have the guts to just jump straight into digital. But with the character designs, a bit less to balance. These are looking good. you nailed a really good since of personality with both characters.
I disagree with just jumping into photoshop always, many prominent character designers draw first. So you could always try being a faster draftsman in general. these are a lot of fun :)