Do Spurs need to sell?

No. And maybe (depending on the price). The chairman, Daniel Levy, has prudently steered a financially sound course in an era of indulgent benefactors and rivals with much bigger cashflows thanks to larger grounds and regular Champions League football. But, as the former Spurs manager David Pleat has pointed out, every player has his price.

Once Real Madrid were prepared to pay Manchester United £80m for Ronaldo, United felt compelled to sell. Senior Spurs sources said at the beginning of what they knew would be a long summer of transfer speculation that the only possible way Bale would be sold would be if he refused to play for the club. We're not quite in that territory yet, but he has made his intentions clear.

Levy has proved better than most at resisting pressure from players and their agents if he believes a sale is not in the interests of the club. Given Bale has three years left on his deal, he nominally holds the whip hand. But in so doing he has sometimes ended up tying his manager's hands by striking deals so late that there is scant time to bring in replacements. Last summer Emmanuel Adebayor, Mousa Dembélé, Clint Dempsey and Hugo Lloris arrived in a late flurry in August as Luka Modric departed.

If Bale goes, what will it mean for Spurs in the long term?

Levy's acumen has succeeded in balancing the books while keeping Spurs on the fringes of the Champions League places. But he faces a huge challenge in realising his long-term ambition of redeveloping White Hart Lane into the £400m, 56,000 capacity stadium he craves to keep pace with the club's rivals.

A new, impressive training complex has been built and work has belatedly begun on the Northumberland Park stadium project. But regular Champions League football is also seen as a prerequisite in terms of income and footballing ambition, which means gambling on wages and transfer fees. Levy would never admit it but Bale's exit might offer a way to square the circle.

On the pitch Bale would be hugely missed but in the swirl of speculation over his future it has gone almost unnoticed that André Villas-Boas, who himself spurned an approach from Paris St Germain to remain at White Hart Lane, has already broken the club's transfer record once (signing Paulinho from Corinthians for £17m) and looks set to do so again for the Valencia striker Roberto Soldado. If he could add more top-class players, Bale's departure could be less cataclysmic than many are predicting.

Can Bale thrive at Real Madrid?

Yes. The caricature of Bale as a diffident ingenu is wide of the mark. Just as he has stepped up to the plate on the pitch, demanding that Villas-Boas play him in the free role in which he has thrived, he is a pivotal character in the Spurs dressing room. Having left Wales for Southampton at 15, then battled back from early difficulties at Spurs as the teenager who signed for an initial £5m, he is unlikely to be fazed at the scale of the challenge. Madrid's new manager, Carlo Ancelotti, clearly believes Bale can slot into his side though, if the deal goes through, it will be interesting to see how Bale handles not being his team's main – at times only – attacking threat.

Can Real Madrid afford him? Is a part-exchange a possibility?

Madrid remain the biggest revenue-generating machine in world football, partly due to individual TV rights deals that give them and Barcelona a huge advantage over European rivals but also through their matchday income and commercial firepower. But they also carry a huge debt (much of it admittedly entirely long-term and manageable) of €590m and remain under investigation by the European Commission over a land deal with Madrid Council. Gonzalo Higuaín has been sold to Napoli for £31m and buyers for other players may have to be found if they end up paying £86m for Bale. Some sort of part-exchange has been mooted, potentially involving the winger Angel Di María and the left-back Fábio Coentrão. But such deals are these days rare in the upper echelons of the game because they are so complex.

Does Bale's marketability have a bearing on his value?

Just as Bale and his team have a clear sense of his worth on the pitch, there is a clear attempt to maximise his value off it. He will appear alongside Lionel Messi on the cover of the next version of the Fifa video game, has signed a lucrative deal with BT Sport and appears on the cover of the latest Esquire magazine. All relatively small beer but, taken in tandem with the crass decision to trademark his heart-shaped hands celebration, it is evidence of a growing desire to create a "brand" around him. While he has nowhere near the standing of global superstars such as Messi and Cristiano Ronaldo, and lacks the cross-cultural appeal of David Beckham, if his game reaches even greater heights, his profile will soar. And as Beckham showed, succeeding as a Briton abroad puts you in an almost unique position. It is clear that Madrid consider this a footballing proposition, however, rather than a marketing one.

Does the "strategic alliance" between Spurs and Real Madrid have any bearing? What about financial fair play?

Tottenham's so-called strategic alliance with the Spanish giants was announced on the same day as Modric's move last summer. If the intention was to soften the blow for Spurs fans, it had if anything the opposite effect, immediately raising fears Spurs would become some of sort of feeder club. The announcement said it would involve the clubs "working together in respect of players, coaching, best practices and commercial relationships". But there has been little evidence of any shared endeavour since.

Villas-Boas wryly revealed he did not have the number of José Mourinho, then the Real Madrid manager and with whom he has previous, when he was asked about it last season. And given that Madrid have apparently spent much of the summer trying to woo Bale from afar, there seems precious little evidence of any special relationship. As far as FFP goes, all of Europe's biggest clubs appear to be simultaneously insisting they will comply with Uefa's break-even rules while shelling out ever bigger sums in transfer fees. There does not seem much evidence of the "cooling effect" that Michel Platini hoped for – if anything Paris Saint-Germain and Monaco, for example, seem determined to drive the market to new heights.

What can we learn from previous Spurs transfer sagas?

There is plenty of recent history to draw on but it provides conflicting evidence. In 2006 Spurs were determined not to sell Michael Carrick to Manchester United but he ended up leaving for a fee that reached £18.6m. Two years later an even more acrimonious saga saw Dimitar Berbatov agitate for a move to Old Trafford once it became clear Sir Alex Ferguson was interested in signing him. Spurs were adamant he was not for sale and reported United to the Premier League but ended up accepting an offer of more than £30m on transfer deadline day.

In both cases Levy had extracted maximum value but damaged the team. Two years later, however, he resisted pressure from Modric in the face of persistent interest from Chelsea and a £40m bid. A year later the Croatian playmaker went to Madrid in a deal worth around £30m. Only Levy knows which of those two divergent paths he will follow with Bale. But given the individuals involved – the player's agent Jonathan Barnett, Madrid president Florentino Pérez and Levy – it will be a tense game of poker in which appearing to claim victory will be as important as the ultimate destination of Bale. Expect it to drag on for a while yet.