I've got a small (roughly like 1ft x 9inchs) dewalt bag with my drill, charger, battery, sawsall, and few other basic tools, I'd like to bring with me soon to keep money coming in. weighs maybe 20lb
That highly depends on how you're traveling and what you intend to use it for.
If you're hitch/hopping with a backpack then I'd say hell no. But if you're rubber tramping then its just a matter of usage versus space.
For instance, I used to travel with a tool bag in my van. I have plenty of room for it but I found myself rarely using it and it ended up just taking up unnecessary space so I left it with family.
If it's something you can see yourself using then I say go for it, if not leave it out