I have a good friend who is a huge Manchester United fan and has an inveterate capacity to always see the positives. I pointed out to him that even if United beat Bournemouth on the final day of the season, they will fail to go above the 70-point mark for the third consecutive year or, maybe not coincidentally, since you-know-who retired and Ed Woodward replaced David Gill.

The last time the club went through such an extended stretch of futility was between 1988 and 1991. "Yeah, but look what happened next," he told me. "We embarked on the longest, most dominant stretch in the history [of] English football. And it began by beating Crystal Palace in an FA Cup final. Funny, that...."

My friend isn't typical of United supporters but he's worth talking to because his optimism and incessant search for positives at least forces you to consider the alternative viewpoint, even though it normally ends up with me telling him he's a bit like Brian.

You don't need to be a football historian to figure out that there is no parallel to be made with the start of the Sir Alex Ferguson era. Yes, those sides were also full of big names, some on the way up, some on the way down (Paul McGrath, Norman Whiteside, Gordon Strachan, Viv Anderson, Mark Hughes, Bryan Robson). There were also talented kids knocking on the door, some of whom would make it, some of whom less so (Ryan Giggs, Lee Sharpe, Giuliano Maiorana, Mark Robins). But there was one key difference: the manager.

Sir Alex Ferguson was in his late 40s at the time. You could see him sticking around for another decade (in the end, he stayed for more than two). Louis Van Gaal is in his mid-60s. Not only does he continually insist that he won't stay beyond a third season (meaning at the latest, he's out of there in May 2017), but he has actually gone out and said that he didn't really want to commit to three years. To him, two were more than enough, but United twisted his arm and made him ink a three-year deal.

(Stop and think about it for a minute. They had an enormous rebuilding job to which they were committing hundreds and hundreds of millions and they actually hired a guy who told him he didn't want to be around after Year 2.)

That's what gets you in this sorry mess. Van Gaal was never a long-term solution and no, the idea that he would have come in, led the rebuilding and laid down the foundations for some kind of glorious future with Ryan Giggs going from apprentice to master is also far-fetched.

Man United's season will ultimately end in disappointment but where do they go from here? Do they even know? Julian Finney/Getty Images

Look at Van Gaal's career. They did win the Double the season after he left Ajax but then suffered through three seasons where they never finished higher than third. Barcelona didn't finish higher than fourth in the three seasons after he left the Camp Nou following his first stint. (His second stint lasted six months and ended in acrimony; you can't blame him for not leaving a legacy there.) AZ Alkmaar didn't finish higher than fourth in the five years after he left them as champions.

The only club where he can claim some sort of legacy (in the sense that they weren't awful after his departure) is Bayern. But this is also the club where he was sacked because they had slipped out of the Champions League places. I'll leave it up to you to decide whether success in subsequent seasons was more down to Van Gaal's "legacy" or the contributions of Jupp Heynckes and Pep Guardiola, or the fact that it's Bayern and they can outspend everyone in sight.

The buzz now is that he may well stay. Depending on who you talk to, he needs to finish in the Champions League (unlikely but not impossible following Tuesday night's 3-2 defeat at West Ham) or wins the FA Cup. (By the way: if they somehow contrive to lose to Alan Pardew and Crystal Palace, it will be three consecutive seasons without silverware or a top-three finish. The last time that happened was more than 40 years ago, when they were relegated.)

You try to make sense of it and your natural instinct is to refuse to believe that Van Gaal's future hinges on whether he wins a single game at Wembley or whether the "noisy neighbours" at City outdo United in terms of futility next weekend. No rational adult would judge success and failure by the outcome of a single game, so you assume that part isn't true. (Then again, this is Woodward and the Glazers: the former's judgement is there for all to see while the latter are silent mysteries wrapped in enigmas.)

You then have to assume that Van Gaal's future is decided on other factors, like whether the side are progressing. Leave results to one side. They're awful by any measure: we know. Sometimes you have to take a step back (OK, a bunch of steps back) to move forward. Leave aside performances, too. Yes, United have rarely played well in the past two seasons and have often appeared fearful, sluggish and ugly to watch. But some argue it's not about entertaining: it's about creating a solid base and besides, if you're successful, the fans will be entertained anyway.

Consider instead whether this team is developing anything resembling an identity on the pitch. This, perhaps, is where Van Gaal has been most disappointing. Personnel and schemes have shifted regularly in classic trial-and-error fashion. It's frankly absurd that after two years, there are only a handful of automatic choices. In any job we go in with a set of expectations and plans and we change them over time as circumstances change. Guys get hurt, guys improve/regress, we have new ideas and we make tweaks. But with Van Gaal, there's no theme.

You can give him a pass on the signings and blame everything on Woodward if you like. After all, that's why he gets paid the big bucks. But it's also tough to understand how you would get the club to commit huge resources on players and then not figure out how to use them. Van Gaal has coached the way you would expect someone to work in preseason: trials, experiments and changes... except we're now at the end of Year 2.

What's the realistic best-case scenario if he stays? Manchester United spend another king's ransom in the summer, add a bunch of superstars, Van Gaal manages to keep all the egos in check, Marcus Rashford, Cameron Borthwick-Jackson and others continue to develop, everyone starts playing really well and win the Premier League, maybe the Europa League, too. (I know it's far-fetched, but we're talking best-case here.)

OK, then what? And then Van Gaal leaves. And then some other guy takes over and you're effectively starting over again unless you happen to find someone who fully embraces Van Gaal's philosophy or unless Giggs has, in the interim, grown in stature and personality to the point where it's a seamless Shankly-Paisley transition. Now, it's possible that will happen, just as it's possible for Leicester City to win a Premier League title. But it's also far-fetched.

Most people seem to understand this. What's tougher to comprehend is what United are doing about it.

Many reckoned Giggs, left, would replace Van Gaal in due course but Woodward, right, has shown little evidence. John Peters/Man Utd via Getty Images

I thought with Jose Mourinho all but camping out on Sir Matt Busby Way with a "For Hire" sign, that would have made sense. Big name boss, spotlight off Woodward's transfer dealings, instant injection of enthusiasm and, likely, better results, good enough for a Champions League spot and a better run at the Europa League.

When that didn't happen, I figured they must be looking to bring in a director of football/recruitment specialist and again, it made sense. Virtually every single top club has one. You'd get a guy who actually has experience and contacts in dealing with agents and intermediaries and wouldn't get repeatedly burned. You'd be freeing Woodward up to do what he does well: running every aspect of the football club apart from the football. And, if you did end up with Mourinho, you'd have a natural counterweight for the Special One's occasional excesses.

Manchester United kept briefing that they weren't going to do this but ruling it out seemed like such a foolish thing to do. I didn't believe them. Silly me. That wasn't it either.

Then what?

Sir Alex Ferguson meets Tottenham coach Mauricio Pochettino in central London. Spurs brief the media saying they're "relaxed" about it because it was a "social occasion." Makes sense. Who wouldn't want to have lunch with Sir Alex? And, besides, while he's a United director, every indication is that he (and, for that matter, Gill) are way out of the decision-making loop.

Still, maybe that's the master plan? Send Sir Alex to sound out Pochettino? After all, that new contract he agreed with Spurs was only a "verbal agreement," right? Maybe he'll come for the 2017-18 season? That would mesh with the other briefing from Old Trafford, the one suggesting that Van Gaal might stay because there will be many more top coaching options available in a years' time.

(A quick aside: Really? Carlo Ancelotti, Jurgen Klopp, Guardiola, Mourinho, Antonio Conte and Jorge Sampaoli are all guys who were available in the past nine months and won't be next summer unless they screw up royally. Do they really think there will be a better batch of coaches around next June?)

The fact of the matter is, we don't know what they're going to do. And that's fine. There's nothing wrong with a club keeping decisions close to their chest. The worrying part is that Woodward doesn't seem to know what he's going to do, either. And at this stage, given his track record, unless he has a really, really good reason (like the Glazers dithering and telling him to do likewise), that's not acceptable.