I am stealing your "Living with.." journals as a text document on my phone for quick access at parties.
Also, as much as I want to hate Boston for having Chara and being so dominant, the fact is that they aren't Detroit. Fuck you for having a juggernaut hockey club.
You will go to Toronto this summer. I need you. By "need" I mean "want to squeeze and tussle your hair a bit."
Talking it out is always the thing to do. If the material is going to be spoken word, then speak it.
If you are actually serious about trying comedy for a bit, create your stage character and write to that. Having your stage character and presence set will make all your writing for it much easier.