I am also "blessed" with 'extra-padding', but typically I do not have many issues when I put on a OWB. My usual carry is IWB with a tuckable from High Noon, and a belt from, well they aren't in business anymore, but its a sharkskin belt. The gun is either a full size 1911 or a Sig 228.
I think the only detail I didn't glean from the thread is which position do you set your holster at? If I am carrying IWB, its usually 3 - 330. OWB I go a little further back, 4-430, and my OWB holsters are canted, not sure how many degrees, but whatever the typical cant is.
Have you tried inquiring at a local leather shop for belt or holster ideas? They might be able to customize something for you, that ordering online might not be able to provide.
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