Having come so close to winning a first title in 19 years, Liverpool need to capitalise on their progress this summer by adding the three players they need (striker, creative/wide midfielder, full back) to win the championship but with Benitez "on holiday", no new chief executive in place and bleak financial prospects, recruitment is going to be tough.
Last summer's top target, Gareth Barry, has already moved to Manchester City for £12 million and Liverpool also look like they will miss out on Carlos Tevez, who may well join Barry at Eastlands.
The speed and conviction with which City are moving is in marked contrast to Liverpool. Then there is Roman Abramovich's renewed enthusiasm for shelling out rubles: Chelsea are threatening Liverpool's efforts to sign England right back Glen Johnson from Portsmouth.
To cap that, the representatives of Benitez's priority target, David Silva, the Spain and Valencia forward, have been in talks with Real Madrid. Everywhere they look, Liverpool are being outmanoeuvred.
Instead of adding to their squad Liverpool have been put on the defensive. Real Madrid, injected with some of the old Florentino Perez machismo, are talking effusively about the gifts of Xabi Alonso. While Benitez was prepared to sell the Spain international at the right price last summer because it would have allowed him to sign Barry, that is no longer an option and, after a fine season, losing the underrated Alonso would be a major blow.
Benitez has repeatedly complained of how tardiness and a lack of conviction has previously cost the club the signing of elite players - Nemanja Vidic and Didier Drogba are the examples he often holds up. Those criticisms were directed, without much subtlety, at chief executive Rick Parry.
Well, Parry is standing down this summer and with Benitez having negotiated a more active role in recruitment as part of his contract extension he must now deliver. There is no doubt that Benitez has scouted players across the world with typical rigour and he is confident that the right hit-list has been drawn up.
But who is going to help him turn targets into signings? Ian Ayre, the effective commercial director, is favourite to take over, but no appointment has been made and, across Europe, deals are being struck.
Another, more drastic problem is that for all Benitez's ambition, he is operating under real financial constraint. The club's accounts, released on Thursday, have called the club's financial viability into question.
Quite simply, they cannot afford to service their substantial debts and, according to one source, could be losing as much as £1 million per month. That means the American owners, Tom Hicks and George Gillett, need to plough in some more of their own cash or find outside investment, and that is unlikely before they refinance their credit deals on July 24.
If this wasn't such a high profile football club the banks would almost certainly not grant Liverpool an extension. As it is, the club will probably get six months.
This will have inevitable consequences on Benitez's ability to spend. The club will be pulling money in through season ticket sales but, according to one source, he has a budget of between £10-15 million – not enough to buy you one top class player, let alone three. Through strategic sales – or even the forced one of Alonso – Benitez might well be able put together one really substantial offer.
Silva is believed to be his priority and it was reported that, while ostensibly on holiday, Benitez met the player last week. Otherwise, reported targets are more modest: Sylvain Distin of Portsmouth as defensive cover, Brazilian striker Kleber from Cruzeiro and Tuncay Sanli of Middlesbrough to add depth to the club's attacking options. Competing for the very top players, as Chelsea, Manchester United and City are, is simply not feasible.
It is not looking encouraging for Liverpool. The latest Deliotte report on football finances, published on Thursday, shows Liverpool fourth in the wage table, paying £90m to Arsenal's £100m, Manchester United's £120m and Chelsea's £170m.
Those are figures for the 2007-08 campaign and since then, Manchester City have come on to the scene, prepared to pay more than any club in the world for the right player.
Liverpool's closest rivals in the pay scale, Arsenal, can offer life in London, state of the art training facilities and a superb modern stadium. Despite claims work will restart in 2012, it is not even clear if the 73,000-seater Stanley Park development is going to happen.
That means Liverpool have to trade on other assets to lure players to Anfield. The most obvious pull is the club's rich tradition.
Then there is the competitiveness of the current team – playing with Steven Gerrard and Fernando Torres must be a draw. Benitez has exploited his connections in Spain in the past, too, to help facilitate deals. But Liverpool can't trade on these ineffable qualities forever.
It has taken an extraordinary effort to get as close as Liverpool did to winning the Premier League, losing only two games all season. How frustrating it would be for that heroic effort on the pitch to be undermined by a slack summer off it.