On my sport standard naked, I'd be able to hide an IWB, but I don't know if I'd want to wear it (I'd feel like an Oompa Loompa with an IWB in my snug Draggins). I'd definitely not be able to hide an OWB with that jacket. The jacket would ride up over the holster and grip.
I'd rather not compromise my gear due to carry method; ATGATT. So far, as much as I can get my head around it, I'd carry in the tank bag. Sure, there are also hassles associated with carrying like that, as well as accessibility during a stop light that might be needed (assuming the scoot away move is take away). The next easiest way to carry would be shoulder rig. But, again, the risks associated with carrying that way is 1, falling on it in a get off (I've broken ribs before and I'm not looking forward to it again) and 2, unless you're in an OC state, the heavy leather jacket can't come off during a rest stop. Riding in TX, I think I'd want a jacket to come off for a breather. We certainly needed it here in the 40* latitude weather.
Anyhow, motorcycle carry is going to be a pretty mixed bag. Not only do you take the regular considerations to mind when choosing a carry holster in general, but you have to now consider gear, bike/riding position and style, and all the other hurts that go with it. What works for one will not work for another. I'd venture to say, motorcycle carry is going to be an extension of ride your ride.
