Hi Jason... happy to see you around here... I am also pretty new to this stuff.. a little over a year... I really enjoy listening to the tracks and playing thru headphones... it adds alot.. unfortunatley.. I have also noticed when I record with headphones on... than listen to the finished tracks without them... well, it loses something... like I record lower with the headphones on so it eventually filters down lower in the end product.. but I have learned or learning to compensate for that...

I use a pair of Sony MDR-7506 ($99.00) headphones I have had for a few years now.. and I can wear them all day long.. comfy IMHO... for all type listening...

this has all been my personal opinion... take it with a grain of salt...