I don't think you can pinpoint an exact moment where it all went wrong but I think it's somewhere around 2012. We got relegated in 2009, maybe slightly unfortunately with a record points total at that time, and then we gave Butcher leeway to rebuild and he did a great job. He then built more and created the cup winning squad that Yogi inherited, the zenith of the club up to this point.
However, during those years when we had regular SPL football, a manageable financial situation (easily recoverable losses, external investment, cup runs, Europe money, transfer fees, money for managers etc) what investments did we make off the park? What improvements were made to the infrastructure of the club, both in terms of facilities for the fans and players? None. We still train at Fort George as far as I can see, the ground hasn't been touched or improved in years, and is now starting to fall apart. We don't have any facilities at our ground like a proper bar or decent food or excellent hospitality.
You can extend this to off the pitch too and this is one reason why I don't entirely blame Morrison and Gardiner for what's happened to the club. We generally operated OK in the top flight, the losses were coverable when they happened and some years we made money. However, we didn't do anything to generate off the pitch revenue, something that coudl safeguard the clubs future. Gardiner and Morrison have taken a lot of stick for the concerts and the battery farm but they've had to do this because there was nothing there before. We didn't even control the land that the stadium is on, IIRC, and were paying money to another company for it. Eventually every club of our size gets relegated and we completely failed to plan for that in any sense - on the pitch, financially, from a business standpoint.
If people remember the summer after we went down it was chaos, we had three different Chairmen, we were releasing players via social media, putting our press releases every day (Twitter account liked porn - statement, Duncan Shearer released by text - statement). It was clear no-one know what to do and really no-one has known what to do since.
Everything that's happened to the club since stems from that failure. The Chairman and the CEO are trying to do positive things but failing because they are hamstrung by issues out of their control as well as their own incompetence. In the meantime the club throws huge money on players and managers, makes massive losses but is at the same time massively penny pinching. Watching the Montrose game via their stream I recall the Covid season where we had one of the worst streaming offerings in the entire league. other clubs have kept streaming and probably make a trickle of cash from it but we huffily insisted ours was fine and now don't do it at all.
The only way I can see this improving is if an outside party buys the club and is willing to invest proper money in it, which I can't see happening or the current backers underwrite another few million quid and we finally manage to claw our way out of the situation we are in, we flukily get a managerial appointment spot on. I can't see either happening to be honest - I fully expect to be relegated and to spend a few years in League One.