but he is waking with wind again now
What is happening with his daytime naps to make you think it's wind?
Daytime naps will always require more effort to get baby to sleep than night time. Daytime naps will be shorter than at night, short naps are developmentally normal.
Add into that the changes that happen to sleep around 4 months old, sleep often gets harder around this time any way and needs more effort to get baby to sleep and stay asleep.
It could be that it's not wind issues causing the sleep issue. It could easily be something else.
Do you have a reflux diagnosis from your GP and reflux medication? This would be a good place to start if not. There are different types of reflux medication and you often have to start with the milder ones before you get the right medication that works.
Once reflux is under proper medical control then as long as you do adequate winding, that should be enough to ease wind/digestion pain.
That, however, may well not make any difference to sleep if the issue is something else sleep related.
How do you get baby to sleep in the day? How long between naps and how long are the naps usually? Where does baby sleep?