Currently I have 2 carry guns, Springfield XDm .40 3.8" and a Ruger LCP. Okay, this is the revolver forum, and both are semi-autos, but that's what I carry. Springfield when I'm wearing a hoodie, and the LCP when I'm not.
However, I have a Ruger SP101 3" that I'm going to send to Ruger and have the DAO hammer installed (pity the 2.25" is the only one that comes with the DAO from the factory). I will carry it in the same spot as my XDM, only it will actually disappear under a t-shirt.
Why wouldn't you get to carry very often? IMO, you should carry as often as legally possible. If you're planning to pocket carry, a pocket .380 (I like the LCP) is the way to go. With the $15 holster it looks like a wallet or a cell phone in your pocket, if anyone can even notice it.
If you're carrying IWB, the Ruger SP101 is IMO your best bet. Yeah, it's heavier, but it's not heavy enough to really bother you when carrying, and it will kick less than an airweight.