For all games as far back as I can remember, the game has been to work out the game and play it. The skill to recognise what you need to do to achieve something in the game and do it is no less of a talent than having the skill to do it straightforwardly.
The online trophies have no minimum DR/SR requirement, you just have to start races on pole, finish races and win races. The PSN trophies don't care if you're an S/S alien or a D/E with fists of ham - or a D/E alien sitting down there on purpose. A pole is a pole and a win is a win.
There are other things in the game which do care - the FIA championships, for example. If it mattered, I'm sure it could have been set to "win 91 races with a Driver Rating of S", but it wasn't.
Even so, some people aren't ever going to get that pole position trophy, because however poor the competition is in their lobby, someone always has to be the worst of the lot. Finding 11 people that this person can outqualify, 65 times, is almost infinitely improbable.