I rotated 2 galco concealables for 17 years. I made a 229 disappear between 1.5 and 2.5 o clock position on my hip.
Having the range of a owb to slide even so slighty along the belt when it's over a belt loop is invaluable. 1.5"-2" forward or back makes all the difference. Can't do that with an iwb while on the go. Doesn't get any more comfy than a good leather owb.
I would never even try getting decent concealability with a paddle holster. Not with anything bigger than say a small .380.
Can you take a pic of you rocking that 229 when were working? No face obviously.