Good question!
As a general policy for myself, I'd rather "figure it out myself" than ask someone else. I also don't have the authority to make purchasing decisions and am a sucker for upgrade salespeople.
Regarding Bentley, well, their website is a pain and it just takes too long for me to "refine" my search of their site pertaining to what it is I need to know - just like using the "help" that comes with the program.
Most importantly, my office runs the Bentley program (is it Microstation? Intergraph? gosh, this is confusing) off a network and I've experienced problems whose only solution rests with the networking (i.e., the Administrators) folks who simply are not at my beck and call. For example, IPLOT requires a complicated set-up that can only be done by our network office. So I give up until they've announced the fix. I HATE getting "your network people will fix it" as an answer. I also HATE having tech support try and sell me something when I need help with a bug that's incredibly unintuitive (like the one I've described).
That is why I am reluctant to contact Bentley.