You need to buy both versions.

This might be a dumb question. If I get the Gold version for MMW will the licence carry over to MMA? or will I need to buy Gold for both versions?

Hi,
1. It really depends on your use needs, if free works then it is OK for you to stay on free version, but over the years and based on user feedback after getting Gold only then they found what it really can do.

2. Getting Gold help us keep developing and improving MediaMonkey so getting Gold is a thanks to us in case Free version is enough for you ATM

I currently have the freebie version of MM. I don't 'rip' a lot of music, mainly because I have like one CD. Everything I had has been ripped previously and is sitting on my external HD. However, I notice that a lot of members of these forums have the Gold version. Is it worth me getting the Gold version, or will for what I use the freebie version be sufficient? As it is I just use MMA to listen to music outside or in bed. And MMW for listening while online.