After reading all of this (several times) I still am not sure what to do.
One thing I do know is that it makes me feel good reading Giles and Olhados post, can't help it. Maybe I should not be afraid of learning Lisp at all. Indeed there is a big legacy and I could get much out of it.
Maybe this is stupid to say but programming in Lisp gives me a specific AutCad feel. I don't know why but if I look at VB or C(#/++) it doesn't look AutoCad at all.
if you plan to make your cad work day easier and like to do customizations, right there on the spot, then auto/visual lisp it is the right tool, it is simple and powerful.