In my last band which was very well organised the singer/guitarist used to do pretty much everything in terms of the gigs/recording sessions/online media etc. I`d look after travel stuff such as planning journey times/routes and booking transport/hotels etc, and the drummer dealt with the merch (which was considerable, think he got the short straw). I think it`s a case of finding someones skill-set then pressing go, or in some cases determining there is no skill-set amongst you for what is required - in which instance then get someone in for that/those tasks. If we had all swapped round with the singer not sorting gigs rather than the 300 plus we did whilst I was in it we`d probably have done 10 - neither myself nor the drummer being in that mould, so identify skills and encourage them.