Having pumped north of £13million into Dundee United since taking control of the club almost eight years ago, Mark Ogren has hardly had much in the way of bang for his buck.The Minnesota-based business leader, who made his fortune from oil, gas and real estate, has experienced what his compatriots might describe as ‘a helluva ride’ at the Tannadice helm.On the pitch, United have gone through six managers, won two Championship titles, suffered one relegation and achieved two fourth-place Premiership finishes under Ogren’s ownership.Off the pitch, the initial £1million he paid for an 86 per cent controlling stake in December 2018 has been followed by his subsequent backing to help offset cumulative losses of around £18million.Like many before him, Ogren has found it difficult to negotiate the unforgiving and often fickle financial landscape of Scottish football with the same level of success he was accustomed to in his other business interests.The 63-year-old, owed £7.2million in interest-free loans by United according to their most recent set of accounts, has freely admitted he is uncertain if he will ever recoup his full investment or turn a profit. Dundee United owner Mark Ogren admits he may never recoup the money he has investedOgren has resisted any temptation to cut and run, however, and those same accounts offered encouragement that the club had turned a corner and are now on the kind of fiscal route he has always envisaged was possible.United posted record turnover of £10.5million and effectively broke even for the first time since he took charge. Significantly, the wages to turnover ratio had dropped to 60 per cent from the ruinously unsustainable 133 per cent recorded in 2019.For United supporters, of course, the only figures which really concern them are the win and loss columns in the league table.It’s why tomorrow’s teatime derby against Dundee at Tannadice – literally the only top-flight show in town this weekend after the rest of the Premiership fixtures were postponed by clubs competing in Europe – already feels like a pivotal game in a crossroads season for the Ogren project.After the managerial merry-go-round of his first four and a half years at the club saw Robbie Neilson, Micky Mellon, Tam Courts, Jack Ross and Liam Fox come and go, Ogren has sought stability in the shape of Jim Goodwin.The Irishman is now the fifth longest-serving manager in the Scottish Professional Football League. Even after Goodwin was unable to prevent United’s relegation following his appointment in March 2023, Ogren stuck by him and saw his faith repaid with a dominant Championship title triumph in 2024 and then an impressive top-four Premiership placing the following year.That momentum stalled last season, however, when United failed to make the top six and there remains a sizeable constituency of the club’s support who are unconvinced Goodwin is the right man to take them forward.After a 1-1 draw at home to Rangers on the opening night of the league campaign when they looked the likelier side to win the game, United were humbled 4-0 by Hearts at Tynecastle the following weekend. The travelling punters did not buy into their manager’s narrative that the scoreline was an unfair reflection of his team’s performance and they made their frustration clear.Last Saturday saw the robustness of United’s defence found wanting again in another 4-0 defeat, albeit against a clinical Celtic side in a Premier Sports Cup last-16 tie at Tannadice which remarkably saw Goodwin’s men hit the frame of the goal five times in a display where they were not devoid of attacking flair. Long-serving manager Jim Goodwin has his critics in the Dundee United supportOnce again this summer, there has been a major overhaul of the first-team squad at Tannadice with 12 new signings so far. It is a department of the club which Ogren had to reconstruct in the aftermath of relegation three years ago and the departure of sporting director Tony Asghar who had become the main target of supporters’ discontent.’From the time I bought the club, everything had been improving season-on-season and, frankly, we got carried away,’ reflected Ogren when speaking after United’s agm last year.’We learned to be more cognisant about what could happen. You can’t control it all. You sit there and try to work out a budget at the start of the year but, as much as you control, there’s a lot more that you can’t control.’Whether you’ll be top six, how good your cup runs will be, matchday revenues, a few of your players could kick on and there’s value there – there are many different factors.’If you are too conservative, you won’t put enough money into the team to be competitive. If you go too crazy, it can go the other way, and you can get hurt by it.’When I bought the club, I said I intended to make money, or else I wouldn’t have done it. Would I have got a better return by investing in something else? That’s a definite. But it was the combination of a return on investment and having some fun and enjoying it – and it has been enjoyable.’I had no idea we would lose so much money. But I can tell you this club can make money – and we’re on a trajectory very, very soon to make money. Can I get a return on the money I have put in? It’s hard to say.’In May last year, Ross Goodwin – no relation to manager Jim – was lured from Plymouth Argyle, where he had earned a positive reputation for his contribution to their League One title success, as United’s new head of recruitment with the focus on a more data and analytics focused approach.Not all of the newcomers have hit the ground running but Australian striker Lachlan Rose already looks like a smart acquisition. United will hope others can step up to the mark and compensate for the departures of key players from last season such as Amar Fatah and Luca Stephenson.The Dundee derby offers the perfect opportunity to make a positive impression. Even at this embryonic stage of the Premiership campaign, victory would represent a major psychological boost for United as it would lift them above their city rivals in the table. Lachlan Rose celebrates scoring against Rangers on the opening day of the league seasonSimilarly, a win for Dundee would see them open a five-point gap between the Tannadice Street neighbours and crank up the pressure on Goodwin.This time last season, it was his opposite number Steven Pressley who was feeling the heat. The former Hearts and Celtic defender’s appointment as manager met with a largely underwhelmed and partly hostile response from the Dundee supporters.Pressley gradually won them around, however, and despite last Saturday’s exit from the Premier Sports Cup in a 3-0 defeat at Aberdeen, there is a greater sense of positivity around the Dark Blues at the start of this campaign.The serious Anterior Cruciate Ligament injury suffered by club captain Simon Murray at Pittodrie was a major blow, however, and it remains to be seen how they cope with his long-term absence.United go into tomorrow’s match in possession of the bragging rights, having won the last derby of last season 3-0 at Tannadice, a victory which helped ensure they finished above Dundee in the table.Goodwin has won three and lost three of the eight derbies he has overseen as United boss so far and taking that record into positive territory would do much to subdue his sceptics among the fan base. It may also help nudge United onto the path of the kind of season Ogren needs to make that balance sheet even healthier.