I had three separate attemps (for travel in March in January, for travel in April in February, and for travel in June in April).
I offered a window of seven days for each portion of the trip (to Madrid and returning from Madrid).
I asked for coach first. When told I could do a rule-buster, I asked about business (why spend 100k miles to fly coach when I could fly business for 90k).
I asked for the direct route in either AA or IB.
Then, I listed options (San Juan, Chicago, JFK, London, Frankfurt, Zurich). It was depressing to be the one listing the options; it was as if they did not want to look.
Eventually, my brother has to do a Madrid-Frankfurt-Chicago-Miami on a date he did not really want, about 12 days removed from his choice. The other oprion is a Madrid-Zurich-JFK-Miami on a worse date... and they would not have even known about those cities unless I mentioned them!!!
Believe me, I am reasonable. I do not expect to call and have the route or date that I prefer just waiting for me. I have been a FF since the late 80's and have booked 20-30 award flights to Europe in that time. Availability (and competency of reservation agents is at the lowest I have ever encountered).

Oh, one more peeve I failed to mention, which I noticed (Am I the only one?):

On the try I mention, I was calling every day. 15 days before the date, nothing available. Then, exactly 14 days before, there is something, not a good route, but I am so frustrated that I take it. Do you know what? That is the day AA starts charging (I believe $50) because it is really close (???) to the travel date. Excellent strategy: Release "free" seats when you can charge (something) for them and they probably are going empty anyway.
Didn't you mention you were able to find something close to your travel date? I bet AA got some extra revenue out of that!!! Goodbye to the Plan AAhead, welcome to MileSAAver (and dollar earner)!!!