RP - Fair one. This has got me scratching my head now. So I consulted Wiki. FA use, of course.
Memory/Myth has it that the cleaners and teachers in Cyprus got the GW1 Gong because, theoretically, the scuds could have reached them, so they were entitled. On that basis I would have said the Churchill earned his bling many times over.
As for the Wings. William Manchester Vol.1. The following may not be from that but from the source that Manchester used.
"They went up as often as ten times a day. Every officer on the instruction staff worried about their eminent student. We were all scared stiff, said Courtney, of having a smashed First Lord on our hands. Eugene Gerrard, later air commodore, said: WSC has had as much as twenty-five hours in the air, but no one will risk letting him solo; if anything happened to WSC the career of the man who had allowed him a solo flight would be finished. Sir Philip Joubert de la Ferte, later air chief marshal, remembered Winston as a very fair pilot once he was in the air, but more than uncertain in his take-off and landing. His instructors usually took over the controls to make the final approach and touchdown. Another future RAF marshal, Hugh Trenchard, gave him lower marks. After watching him wallowing about the sky, as he put it, he decided Winston was altogether too impatient for a good pupil.
But Churchill persevered. He spent the afternoon of Saturday, November 29, 1913, in the air with Captain Wildman-Lushington of the Royal Marines. After they had parted, the captain wrote his fiancee: I started Winston off of his instruction about 12.15 & he got so bitten with it, I could hardly get him out of the machine, in fact except for about ¾ hour for lunch we were in the machine till about 3.30. He showed great promise, & is coming down again for further instruction & practice. Winston himself was dissatisfied. Once he had set his mind on an objective, anything short of total conquest was unacceptable".
True doesn't prove that he got his wings but I can't be arrsed to read it all.