I have a BA amex which works similar, and it was the annual fee one too that means you need less miles to get perks and get more per £ spent and it still doesn't make sense. Even if he put everything on it, he wouldn't have enough. Not for the amount he flies. His life isn't that elaborate. Maybe if everything he spent on that book he might have enough as a one off. But then he is just chasing his tail financially as he isn't earning the money back from sales and ad revenue.
To get long haul flights, especially in upper, you'd need 100's of thousands of air miles a year to keep that up.
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Just having a look at the virgin credit card. You can only get one upgrade or companion voucher per year. You have to spend £20,000 or more in one 12 month period to earn one.
So even if Adam is spending 20k a year, he is only getting one upgrade voucher.