One thing to check for, especially since you're use to IWB carry. Put the OWB rig on and try reaching up high like for something on a top shelf. OWB carry requires a longer cover garment at times like that. I carry a cane left handed (weak side) so any reaching (i.e. for groceries) is done with my strong side hand.
Yes, OWB CAN be more comfortable but that's not always the case. It'll depend on your belt, holster and gun you're wearing. I carry my Glock 19 primarily OWB but my 1911s IWB because of their thin profile.
Give it a try and see what YOU think.