There's certainly a point at which it's fair to just go ahead and ask, and I can absolutely understand spending less time searching if your question is extremely specific to your own situation. I definitely don't want anyone to be afraid to post on the off chance their question was already asked!
It's just a matter of doing your due diligence. If you don't find your answer reasonably quickly, you should feel fine posting! Just remember that community members and staffers who answer questions have often already spent quite a lot of time answering the same, more general questions over and over.
But, again, if you're not finding an answer within a few minutes, by all means post a new thread. We and the community are more than happy to help. 