Yeah so VoiceMeeter might be easier to setup and more straight forward. Baically you see the buttons with A1/A2/A3/B1/B2? Well you can mix and match any input you have with any number of outputs. So you can have one for grouping sounds you want to hear (say A1), one group with sounds that you send to your friend on skype (A2). and then the remaining busses you can use to send individual tracks to OBS where you select them as inputs and record to their own track.
And oh, if you don't have "proper" ASIO drivers I do recommend you try out ASIO4ALL. While it's not needed for VoiceMeeter to work, the programs that actually do have ASIO support greatly benefit from the reduced latency.