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Great post, dicion. You took a rather humorous real-life experience and joking follow ups (which are all great, don't ge me wrong) and were able to spin it into something useful to all who use CHL. Really puts this all into perspective. And I also find great benefit in any situational mind games one can use for training the brain for similar real-life situations.

If I encountered the same guy at the party, I also would not have mentioned my own guns (in addition to stated possibilty that he's casing the place looking to steal, any mention to any other person that "I have a gun" could be construed as a threat - we all know this is not what OP's friend meant, but why run the risk that not everyone thinks as we do about such things?). I likely would not have made the flippant remark at all - why antagonize the guy? You'd be amazed how quickly some minor perceived slight can set some guys into "I'm gonna whup your ..." mode. Probably would've just ignored the guy. But also would've made a mental note ... guy says he's a two-time con, so good at martial arts his hands are "registered as deadly weapons"; so if this guy corners me in a dark alley and demands my wallet, I'm shooting first and asking questions later.

Capability: yes, he says he can kill me with his bare hands - and he's committed crimes before
Desireabilty: slightly grey area, but anyone with the capability to kill me who is committing a face-to-face crime (robbery) is potentially a threat to my life
Ability: he's there, just me and him, in a dark alley, and he's demanding things ... so yeah, I'd say he has the ability

Another way to phrase the above three steps that I've always used (and that you hear in TV cop shows) is ..

Means
Motive
Opportunity

Basically means the same thing as previous three key words.