John Henry said that not qualifying for CL would be "a major disappointment." If we already had one of the highest point totals with the squad we had at the end of last season, then we only should have gotten better. Henry said he wanted CL.
Agree with the bulk of you post, but wanted to touch on the bit in bold. Sure, it's disappointing to miss on CL again, no argument from any of us. But this was said before the season began and he didn't have a crystal ball. The top people at the club thought that the players they bought would do the trick of nicking a top four finish, but they didn't (and I think it's unrealistic to think that they would from now on). My take on this, and I have said it at the time, is that they didn't buy top players, they bought 'sufficiently good players' that will help us reach the set target. Borderline 'sufficiently good players'. But that wasn't good enough, and so much was already clear by January, wasn't it? And yet they didn't dip into the transfer market... So, yes they were disappointed, but not quite devastated, because another thing was also clear before the January transfer market closed - we were in a cup final (and they thought winning against a Championship team would be easy). I'm sure that winning the Carling Cup makes up for the miss on top four in some way.
You've also raised the question how are we going to attract top players without CL football. My answer is with trophies. We already won one and have a chance for another one. CL football is where every top player wants to play, I don't mean to downplay the competition, but it's not everything. When a player retires, he'd look back at what has he won over the length of his career. And let's examine the teams from the top leagues that have played in the CL but have won no trophies over the last 4 years (the average length of a player contract):
England: (we would have been here if not for the Cup), Arsenal, Spurs, (City would be here, but they can win the PL)
Spain: Atletico Madrid, Valencia, Villareal, Sevilla
Italy: Roma, Fiorentina, Juventus, Napoli, Udinese
And the list can go on and on to include other leagues...
Excluding financial reasons, which always play a role but are not related to the footballing reasons I'm laying out, there are only a handful of teams less attractive to players. In England that's United, City and arguably Chelsea, In Spain - Barca and Madrid, and in Italy - the two Milano grands and Juventus. So, if you were an ambitious player and wanted to win trophies, would you like to play in the CL with the teams above or would you like to win medals that you can show your kids? Players choose different things, some of them money, some the London lifestyle, that's understandable, but we don't need to attract those players.
The big difference is that winning this Cup took us out of that pool and put us in another - the winners pool. Arguably, any of these teams above can win a domestic cup and will gain some appeal, but we are there now, and we have to show that we're reforming and we're going places; it's not one off. That's what we have to sell.