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Im struggling doing this one :|
Whats the best car to use for it? And should it be A-Spec og B-Spec?

Also my A Star Is Born hasn't unlocked.
Would I need to train a new lvl 30 b-spec driver to get it, or can I just level one time with a driver over 30?
I got lvl 40 trophy, but from another save etc

I had a struggle with this too, especially in A-Spec because at least one opponent would use the Chaparral 2J "washing machine" car and win by several car lengths.

For the trophy I'd do the race in B-Spec with an experienced driver (preferably at driver class 30 or above). It doesn't matter which car you use, they're all just as good as each other I find, I got the trophy by using the Jaguar XJ13, bought the few remaining upgrades and did a bit of tuning. My B-Spec driver won the race by 5 seconds.

As for "A Star Is Born", I got the trophy for real but when I tried on a jailbreak PS3 with a new user with one of the saves from this site, one driver levelled up from class 36 (I think) to class 37 and the trophy popped. Might be worth a try.

I Got the Dream Race Trophy using the Ford Mark IV Race Car on Expert Series/Historic Racing Car Cup/Deep Forest Raceway with a few upgrades.
I did this on A-Spec, although it may be quite a challenge, it is do-able.
Once you take the lead you can easily block out the 2J & 2D, just don't make any mistakes and you can win no problem.