Part of your problem might be your airline hookup.
Air compressors generate a lot of heat, so the air coming out of your compressor is pretty hot, so your putting hot air directly into your filter, this doesn't give it time to cool and turn to water, so, some moisture might be getting through your filter, maybe more then the last filter you have on the spray gun can capture.
You can't get rid of the water in air lines, you have to trap the water.
The more time painting the more your compressor runs and the more water you generate.
This should help a lot if you can do it.
If you could put in 10' or better yet up to 50' of something like 3/4'' black pipe.
So a couple of feet of flexible hose right out of the compressor, then into some black pipe, then into your filter, then into the rubber hose.
The pipe will cool off the hot air and turn it into water, so you want the black pipe at an angle going along the side of the wall, probably up as it leaves the compressor, then as the water cools it will go back into the bottom of the compressor.
I'll put up my drawing of the big picture, and if you look at that it will help give you an idea on how to go about it.