So long as we understand that I'm on a different continent...
Me: "What level do you require?";
You: "Anything below ten thousand (or FL210 or whatever)."
Me: "Do you require an IFR or VFR clearance?";
You: (Be truthful. It simply isn't my place to suggest.)
Me: "Would you prefer to route East or West of the overhead?"
You: "No preference."
If you've got needs, pipe up and we'll work it out. If you don't care one way or another, say it in clearly and we'll work it out. My only request is, if you DON'T care one way or the other, be brief when you tell me. Also remember, if I'm giving you options (i.e. "east or west of the overhead") then that means that either one is good with me. If it wasn't, then I'd have already pinned you down to a particular routing. I'm NOT going to offer you something that's going to make a mess of things.
And as to your final question... sometimes, yes. Especially if it takes a long time for you to say it. Again, if you ask for something that's not going to work for me, then you're not going to get it and I will suggest an alternative. So, bottom line: tell me what you want and we'll discuss it.