I look at them at most of them as long term signings - Carroll (22), Henderson (21), Adam (25), Enrique (25), Coates (20). Have a look at how they're doing in three years time and then judge whether it was money well spent.
The signs with Carroll are all incredibly worrying right now. He looks slow, weak and shit. It's pathetic.
Henderson is a player we didn't really need right now, but I think it will turn out well anyway. Adam is what he is, a decent midfielder with dead ball skills. He needs to adapt his game a bit but he's a reliable enough sort. Coates is a highly promising centre back.
The way the Premiership is at the moment it's unrealistic to expect us to challenge for the title every year , we could only do that by consistently overspending. So the sensible thing to do then is to buy players with a specific window of opportunity in mind (probably starting in 2012). Taking into account the expected development of the likes Shelvey and Sterling and maybe a couple of others, along with the signings we've made recently - if things develop as people think they might (and Carroll turns out fine) we've got the basis of a very good side and time to add to it.
It's that line of thinking that has me convinced that Downing is a massive waste of money, I think he's going to be shit in three years time and will need replacing. So for me it's 20m we've wasted to make us a little less mediocre while winning nothing. Contrast that with the signing of Bellamy - he makes us a little better but doesn't cost us a fortune. Two stopgap signings, one example of how to do it well and one example of how not to do it. I would have preferred to keep Meireles but again I don't think he'll be up to much in three years time, so I'm not that bothered.
I definitely think right now that we overpaid for Henderson, Downing and Carroll - massively so, but I think we're still giving ourselves an opportunity down the road to challenge. There seems to be a plan in place, it may not work but I think we're actually approaching the task sensibly for the first time since I reached adulthood.
Essentially the signings weren't designed to make us immediately better, so I'm not going to get all upset about them just yet - even though I am beginning to hate Andy Carroll.