There's a flaw in your maths.
New card for £300 less selling your old one for £100 = £200.
2nd hand card = additional £100 and so only £100 saved.
or new 2nd card = additional £150 and so only £50 saved
But point taken about 2nd cards. That's why so many people picked up a 2nd cheap 8800gt to have 8800GT SLI which was very potent.
In the idea that second hand cards go for 50 quid under shop value:
Okay let's say you buy a 5850 at 200, and it comes down to 150 quid. The 5870 has also come down 50 quid.
You flog your 5850 at 100 pounds, and are able to put up another 100 for a 5870 totalling 200 (second hand value) and costing you in reality 100.
You've practically bought this 5870 for a release worth of 300 pounds now.
On the other hand you buy a second hand 5850 at 100 pounds to crossfire with your current one.
You've now also spent 300 pounds in total but have better performance than the 5870.
Keeping with the idea that the cards go second hand 50 quid under what they are in the shop;
The 5870 comes down another 50 to 200 pounds, you're able to sell it for 150 pounds. A new card is out costing 300, you put 150 with the money you got for the 5870 and purchase the new card. Forgetting all previous money spent, you've bought this new card for 150 quid.
The 5850's you previously crossfired are likely to have similar performance as this new card much like the 4870s have with the 5870 - so no upgrade necessary.
You're now back at starting point. The crossfire 5850's have little value - 50 quid each. The new card you've bought will have greater value but you've already spent 150 quid extra to obtain it.
Assuming you sold both the 5850's as soon as you crossfired them, and the new card you just bought as soon as you bought it.
You sell the 5850s 50 quid each for a total of 100 pounds.
The new card for a total of 250 pounds - deduct what you bought it for - 150 pounds, and you have gained back 100 pounds.
Complete neutrality.
And the cycle starts over.
Buying new, 2 cards are better than one.
Buying second hand, it's pretty much level ground.