I read this as "It's okay if I give it to people who wouldn't buy it..but only if they're cool with iTunes." I'm not jumping to conclusions, am I?
Anyways... No worries... I have a (potential) solution that fits your bipolar stance on ip theft and apple software (see attached pic).
How bout I send you $1 on paypal. Then you can turn around and pay an additional dollar with a new iTunes account.... since apparently that's no big deal and super convenient... and after all that, you can email me the DRM free file feeling warm and fuzzy knowing that this truly is me not wanting anything to do with iTunes and nothing else... and I'll get the benefit of purchasing/listening to it without having to deal with the software, new account, and allowing them to sew me into a human centiPad (sorry.. allegedly... South Park may have exaggerated that one).
Just keep in mind that if you take the dollar and send me the file without purchasing it again that you'd become the true d-bag by getting paid for someone else's work.
What do you say? Want to bury the hatchet and be friends? Can't we all just get along? Doesn't that make you feel better?