Newbie Help - Hobby vs Bridgeport

I would like to delve into learning about CNC machining.

1. I currently have an older Bridgeport mill and would like to know if I
would be better off "automating" it or should I try to build one of the
"hobby" mills first.

2. If the answer is the "hobby" mill first, are there controllers that I
could use that could be used to drive the Bridgeport should I wish to go
that route later?

Thanks
Scott