It's been a busy transfer window, especially for Manchester and London. Some teams added to their squad early, some waited until the last minute to recruit new players. Not as busy as 2 years ago, but still very busy with City, Chelsea, Liverpool, QPR (it seems), Blackburn, Leicester, Roma, Malaga, Real Madrid and Manchester United all spending fairly heavily.
There's a lot of bias on this thread, but I'll try and be non-biased (I added some of my own 'awards' as well):
Best Transfer - Ashley Young. He's a top player and exactly what United need to win the Premier League again. He compliments the strikers with his sublime passing and he can score a few goals too! Juan Mata, Sergio Aguero and Phil Jones deserve a mention here too!
Worst Transfer - Rob Elliot to Newcastle. The former Charlton No.1 is by no means Premier League material despite Newcastle needing a third keeper. Ok, maybe he was good in League 1 but doesn't that really deserve a move to the Toon? David Goodwillie and former Hammers defender Danny Gabbidon aren't great signings for Blackburn and QPR either!
Best Value For Money - Simon Vukcevic - For only £2m, he is a steal from Portuguese giants Sporting Clube de Portugal (Sporting CP). A fantastic attacking midfielder, the Montenegro international has been a consistent performer in Portugal for Sporting. Shane Long, Michel Vorm, Seb Larsson and Brad Friedel also represent great value for money too.
Worst Value for Money - Jordan Henderson. A promising youngster who has a bit of potential, but he is not worth £20m - his value is probably around £5m. A good player who may turn out to be great, but I am saying he is overpriced. However, I don't think he's as bad as everyone thinks he is! I may surprise everyone with my next choice, but I also think Sergio 'Kun' Aguero and Alex Oxlade-Chamberlain are overpriced. The former is obviously a fantastic player, but not one who is worth £40m. He could be a top scorer, but if you compare him to players like Darren Bent (~£20m) and Javier Hernandez (~£5m) it looks ridiculous. Oxlade-Chamberlain is inexperienced and no matter what his potential is, £15m is a lot to pay for a 17 year old.
Dark Horse Transfer - Shane Long, Yohan Cabaye, Seb Larsson and Romelu Lukaku. All good players who were relatively cheap, bar Lukaku, and should perform above their low expectations.
'I Hope He Fails' Transfer - Yossi Benayoun (if he leaves, which looks likely). He played well for us (Liverpool) as a first team player yet he ditches us and goes off to Chelsea where he hardly gets any first team football with the Blues favourite Frank Lampard in attacking midfield. And now he is being exchanged for other players.
'I Hope He Suceeds' Transfer - Owen Hargreaves. It's always saddening to see a player of his quality being destroyed by injuries. Same goes for Jonathan Woodgate.
Best Buying Team - Newcastle United. The Toon have made some shrewd deals this summer, including Sylvain Marveaux and Davide Santon. They now look capable of pushing for a top half place this season.
Worst Buying Team - Swansea City. Maybe Wayne Routledge and Danny Graham are good players, but are they worth a combined fee of around £5.5m, when the money could of been used to buy Davide Santon, a quality full-back? I don't think so.
Best Selling Team - Arsenal. Getting £25m for Samir Nasri, who only had 1 year left on his contract and £40m [what they originally wanted] for Cesc Fabregas was some great persuasion by Arsene Wenger.
Best Promising Youngster - Romelu Lukaku. This guy has obvious potential and it'll be up to Andre Villas-Boas (and Didier Drogba, it seems) to nuture it and make him into a formidable player.