is it really random, or is there some trick I'm missing? just kinda wondering; sometimes there seems to be a pattern to the answers, other times not so much :P

It is totally random. This been confirmed by staff.

In addition to that, I've confirmed it by experience as well as several others. Many times you get the exact same question with the exact same item options and you get different results.

Like every other game on site which is random based (like Crypts, ice fields, safe cracking, etc), I choose a pattern and stick with it. I haven't been completely successful yet, but I have managed to get the Level 5 achievement, so I figure I'm doing okay.

awesome, good to know! thanks for the help! :)