I was pretty hefty a few years back. Not 250, but I was 215-220 on a 5'6" frame wearing 38" pants.
I still wore what I wear today, mainly a Blade Tech IWB with a reload on my belt. The only thing I've changed, has been my pants size. (I'm 160 and a 32" now)
IWB takes a little while to get used to no matter what your size is, so dont think your size is really necessarily an issue. It takes a little while for you body to get used to the gun being there, especailly if you dont change your pants size, which I dont. I wear my normal size pants and have always been more comfortable doing so, as the gun moves around less and stays in place. It feels a little snug at first in the morning when you put them on, but soon feels fine as the pants give a little.
For IWB holsters, I've pretty much settled on the Blade Tech and a Milt Sparks VMII, with the Blade Tech being used the most. If you sweat, the Blade Tech is the better choice.
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