Be careful what you ask for. Labour relentlessly demands a general election, and may attempt to bring one about in the autumn, but is the party in good shape to fight what will be one of the most critical campaigns in our modern history? When I put this important, yet neglected, question to one senior figure in the party, he responded with blunt candour: “No, we’re not ready. Not remotely ready.”

Let’s break it down into five components: candidates, leadership, messages, mobilisation and money. In each category, Labour faces difficulties. Some are relatively mild. Other handicaps are severe and hard, even impossible to address in the very little time that may be left before an election is upon us.

Labour will be outgunned financially. Tory donors who went on strike during Theresa May’s tenure are opening their chequebooks for Boris Johnson. The Conservatives won’t have a problem spending up to the £20m limit on election campaigns; Labour sources believe they won’t get close to that figure. High-value donations have dried up under Jeremy Corbyn. That is not surprising – his remaining devotees would probably say that it is a virtue – since Labour’s policies are not friendly to wealthy individuals. The lack of high-value donors was compensated for by the surge in the party’s membership during the “Oh, Jeremy Corbyn” period. The party started working on the basis that this would endure and set budgets on the assumption that it would have a minimum of 500,000 members.

As adulation of Mr Corbyn has deflated, so has the membership. Party insiders report that the number has fallen below the half-million mark, unravelling those budget assumptions. The trade unions will try to help out, but their ability to do so has been crimped. Union political funds were depleted by the 2017 campaign and Tory-introduced changes to the law, which requires new recruits to actively opt in before some of their dues can be put in a political fund, have made it harder for the unions to throw a financial lifeline to Labour.

‘Louise Ellman, the last Jewish Labour MP on Merseyside.’ Photograph: Sean Smith/The Guardian

When an election is on the horizon, any party likes to have well-established parliamentary candidates working closely with local activists and using every ounce of their combined energy to prepare for the contest. In an act of spectacularly terrible timing, the Labour leadership has chosen this autumn to unleash what one shadow cabinet member predicts will be “mayhem” in local parties. Beginning in September, all Labour MPs will be exposed to potential deselection, a process that starts with a “trigger ballot”. This is a sort of confidence vote and, when lost by an MP, it can pave the way for their removal. This will happen in three waves. In London, Neil Coyle and Margaret Hodge will be in the first wave. It is surely not a coincidence, as the old Marxists used to say, that both these MPs have been fierce critics of Mr Corbyn. On Merseyside, some well-informed observers think that every single Labour MP, except Dan Carden, will be threatened with deselection. That would include Louise Ellman, the last Jewish Labour MP on Merseyside.

The struggle to defend themselves against trigger ballots is consuming the energy of Labour MPs and dividing local parties, just when they should be preparing to do battle with the Tories. The rules and how they should be interpreted are open to dispute, so there will be challenges, legal and otherwise, by Labour MPs targeted for eviction. Some may decide to stand as independents, splitting the Labour vote. So Labour faces the prospect of heading towards an autumn election in the middle of a rancorous and divisive deselection process that will make the party look vicious, fractured and incompetent.

We already have an excellent idea how the Tories will fight an election. They started megaphoning their messages from the moment Boris Johnson stepped into Number 10 and put his party on a campaign footing. The Tory trio of key messages will be on Brexit, crime and the NHS. These are the issues that usually come in the top three when pollsters ask voters what concerns them most. The Tories don’t expect to win on the NHS; they seek to neutralise it as an issue. On law and order, where Mrs May was vulnerable at the last election because of cuts to police numbers, the Tories are striving to reassert their traditional advantage and hope a hard line on crime will help push Brexity Labour voters into the blue column. On Brexit, they look to attract the no-deal and let’s-get-it-over-with segments of the electorate. Tory staffers have been told that all leave is cancelled.

There’s no matching sense of urgent preparation for an imminent election on the Labour side. A summer of listless campaigning has not clarified what messages the party wants to prioritise. Labour is also struggling to settle on a sustained line of attack against the new Tory leader. Emphasising an “anti-austerity” theme worked well in 2017, but the worry of some on Labour’s frontbench is that this will have less salience when Mr Johnson is splashing around cash on schools, health and the police, even if it is often funny money.

Ian Lavery: ‘ferociously opposed’ to Labour shifting to a less equivocal position on Brexit. Photograph: Will Oliver/EPA

The largest and most unresolved question for Labour is whether it will fight a Brexit election as an unequivocally anti-Brexit party. If an autumn election cancels the party conferences, the manifesto policy will be decided by what is called a “Clause V meeting”, composed of the shadow cabinet and the national executive committee, the latter dominated by Mr Corbyn’s allies. A less equivocal position on Brexit might recoup some of the disillusioned voters who have migrated to the Lib Dems, the Greens and Nationalists. The party chairman, Ian Lavery, and Len McCluskey, the general secretary of Unite, are ferociously opposed to making that shift. Others fear that it is simply too late now. According to people who have seen it, the party’s private polling suggests that many Remain voters will doubt the sincerity of a last-minute conversion.

Mobilisation, the capacity to get out your supporters on polling day, matters a lot. Even after a decline in its paid-up followers, Labour still has many more members to send out on to doorsteps than the Tories and has historically performed well in what strategists call “the ground war”. The anxiety is that most of those who were in charge of the successful ground effort in 2017 have departed Labour headquarters, which has seen a large exodus of experienced staff in the past two years. Social media was a vital tool of mobilisation at the last election. Labour was far superior at using cyber-campaigning to rouse supporters, propagate memes and create political dividing lines to the party’s advantage. Labour cannot rely on having that edge again. From the moment Mr Johnson arrived at Number 10, the Tories started testing reaction to Facebook ads featuring him. The Vote Leave campaign veterans who now populate Number 10 and Conservative campaign headquarters are ruthless exploiters of digital politics, where there are few laws to regulate behaviour.

Which brings me to leadership. A Tory campaign headed by Boris Johnson will obviously be radically different to the hapless effort fronted by Theresa May. Tories regard him as an infinitely better political salesman and so do many senior Labour people. “He could hardly be worse than her, could he?” remarks one shadow cabinet member. He is much more of a Marmite politician than she was, which is a source of Labour hope. “We will be able to mobilise our supporters’ loathing of him much more than we could against May,” predicts one Labour campaigner. Against that, Labour’s appeal to the country will be led by another Marmite politician. And Mr Corbyn is not the novelty he once was. He is much better known to voters than two years ago and what they have learned they have generally disliked. When asked who they prefer as prime minister, he is easily bested by his Tory rival.

His fans will respond that nearly everyone, including me, underestimated the Labour leader’s ability to turn around a campaign in 2017. Maybe he can be Comeback Corbyn again and surprise everyone a second time. It would be arrogant to categorically assert that he can’t. It is, though, fair to point out that every poll conducted in the past four months has given the Labour leader a negative approval rating of -40% or worse. Even Jesus Christ only had the one resurrection.

I don’t know how an autumn election will end. I do know that this is not an encouraging place for Labour to start. Most of the party’s senior personnel know it too.

• Andrew Rawnsley is the Chief Political Commentator of the Observer