Firstly, very good post, Storts. I don't agree entirely, but for the most part it's bang on. In fact, I agree with almost all of it apart from the fact that I think I'm a bit more optimistic about the future than you appear to be. I disagree with Gate that the money spent meant that missing top 4 is a failure. We only had that money because we'd lost our 3 best players over previous couple of seasons. It is difficult to replace Bale and Modric (and to a lesser extent, van der Vaart) and expect to get stronger. However, the fact that the vast majority of the Bale cash went on Lamela, Soldado and Paulinho, none of whom have done much.
I'm not overly pessimistic though, with one huge caveat: a high quality manager must be brought in ASAP. As Storts mentioned, the club has been the gong show this year. I agree about Vertonghen's attitude, but he must look at what's going on in the boardroom and on the training field and wonder what the hell is going on. We need a manager with a clear strategy, good people skills and more support from Levy.
Here's my squad breakdown:
GK - We need someone with a reputation and gravitas to convince Lloris to give us one more season.
DEF - For as long as I've posted on this board, every transfer window I've listed fullback as a primary need. We've played this season with Rose and Naughton who are so far away from being Champions League level fullbacks it's ridiculous. So we need 2 - 3 new fullbacks and we probably need to spend big on them. Dawson's not good enough. I was gutted when he turned downn the QPR move and feel vindicated by his performance this season. Seems like a great guy and a club man, but unless he can drop his 40 time by half a second or so he's done. We need someone to motivate Vertonghen. Probably need 2 more centre backs. Shouldn't have sold Caulker. We need someone to give the players a game plan to follow and defensive tactics that don't result in the countless stream of calamities we've seen this season.
MID - The midfield has looked confused and hesitant all season. As Storts lamented, Lennon has been dross. Townsend should be on the left. I'd be happier if he were a bench player next season though. Whoever manages the team next season needs to work out where Lamela fits. I agree with building the team around Eriksen at 10, and Lamela should be part of that gameplan. Paulinho looks like he's been scared of getting injured before the World Cup. I hope he doesn't make it now as a result. Sandro may not be great on the ball, but he's a defensive force in the middle and can pass pretty well. He plays well with Dembele and vice versa. We really needed to pressure a lot more in the centre of the field this season and these are the best pair for doing that, by a country mile. Bentaleb looks pretty promising and hopefully this experience has done him some good. Hopefully the flak that's been directed his way doesn't get to him. He does look like a red-card liability though. A few dodgy tackles/stamps this season that he needs to sort out. Chadli has been alright. He's young and should be perservered with. Can't shoot to save himself, but heck, that sums up almost everyone at Spurs right now. Sigurdsson is decent as an impact sub. He's not afraid to have a shot, which is something we could do with more of. I don't think that the midfield, as it stands, needs a lot of attention, but Lennon and Paulinho are replaceable if they are going to perform like they have for most of this season, and we could do with a winger or two.
The forwards have had very little in the way of service all season. Soldado has had some terrible games but also some pretty good ones. He's clearly not Suarez but his season was reminiscent of Suarez' one a couple of years back when he was doing everything pretty well but not putting the ball in the net. Adebayor has been fantastic. I'm not sure if we can keep him next season though as I'm sure that City were only paying half his wages for the first 2 years. The fact that you don't know what you're going to get from him probably makes Levy reluctant to pick up the rest of the bill so he'll probably be sold (if this is indeed the situation). Having seen some of the highlight packages I wonder whether Lamela might be suited to playing up front in a 2 man attack. Regardless of whether he can or not, we will probably need to add a striker, especially if Adebayor can't stay.
TL

R = I think we've got a decent squad but there was no plan at all this season and the club appears to be being run by a bunch of goat herders. While it didn't help that half of the squad were new, the players attitudes were affected by this and so a reputable manager MUST be appointed ASAP to get the best out of some decent players. Apart from the backs. Most of them suck. Levy will NEED to spend a bit more than he's likely to bring in through sales this season. He'd better bloody do it for once.