Things would be a little different if Spurs had qualified for the Champs League when we had the chance to do so a few years back. Although the distraction of it might have meant us failing to get there the next season (not that anyone would have complained that much). The 4th spot position would have mean (in such a scenario) that we could attract second-tier world class players because of what we have to offer on the European stage.
With regards to the current Keane/Berbatov situation, Spurs have to yo-yo through this type of transfer disloyalty until we strike lucky, which means regardless of us losing our 'best' players every 2/3 years to 'bigger clubs' we have to be in a position where we can still challenge for 4th spot - even if it means finishing 5th - and picking up a Cup or two in the mean time.
The luck part is down to one of the current Big Four having a mare of a season.
So, in conclusion. We have to be better than everyone else as a given, and then concentrate on aspiring to break into the top four.