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The general rule of thumb is if the owner of the IP isn't a big name company you go out of your way to get permission, otherwise it's not a top priority thing because most big name companies don't care unless the work is being mass produced. In that instance, expect a cease and desist.
A lot of big name companies see fan work (sold or not) as promotional work, even though according to the law (US law, at least) all forms of fan art are copy right infringement.
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From a UK standpoint, I'm pretty sure that non-profit fan art is perfectly legal here. If you sell and make money however, then that profit is seen to have been effectively stolen from the IP owner, and at the least you would be ordered by court to pay it back in full (and likely cough up both parties' legal fees too).
I suppose it's a risk either way. But you're quite right, big companies wouldn't really bother themselves with a few small one-offs. Probably wouldnt even get a reply if you asked permission.