You know, M, that brings up something that really pisses me off. It's the "guru" mentality that squashes questions with nothing more than intimidation tactics. If a person is passionate about training and fitness they will RELISH the oppurtunity to avail you of their ideas. And not with a one-size fits all one line response.
If someone tells you you are overthinking that usually means they have no answer! Sure, people over-analyse simple things all the time...that is a different story. But when you are paying someone they better have the answers even if it is to explain to you why it's the wrong question
A trainer should be able to explain the reason behind every single thing they prescribe and be ready to back up their plans at all times with thorough explanation. When it comes to your health you are not "over analysing" when it comes to questions, you are being smart.