Sorry for so many Qs Hun....I know sometimes it's impossible to know what's going on, t woke a lot at this age and when this frequent it was always pain

has he been worse since solids were estd?
How's the milk increase during the day going? How's Js reflux/meds etc?
I guess if you think it's pain there isn't a lot you can do but try to eliminate it. If no pain then do you think he needs some more st?
And, like Ali mentioned, you may have to either expect rubbish naps on the go or stay in. I always stayed in as I hated T not napping and he never napped in the car or buggy