I'm not looking into your finances from years ago, I'm telling you why the new rules effectively prevent that happening without the need for what ever it is he did to be banned. If he loaned you the money to cover the losses, under the new rules it would be pointless because you'd still show a loss and be penalised, so why bother doing it when the end goal will be blocked? If he put the money in as capital he'll have done it by increasing the shares issued and then buying them back. If it's done that way, again it doesn't impact on profit and loss, so there's no point under a break even rule of doing it.
Say a team needs to be saved from relegation, say the owner loans the club £10m to buy players to keep them up accepting whatever punishment there is would be better than relegation. Say they go down anyway and the owner takes his money back and leaves. Maybe theres other loopholes but wouldnt you agree its better to close any loopholes than leave them open for an owner to exploit?
You make the punishment relegation if relegation has been avoided as a result of the overspending. By the time the accounts are out you're well into the next season, but you just make it a default relegation at that point, and over 50% of the TV revenue and prize money is yet to be awarded so you give that to the teams relegated in their place (like West Ham paying Sheff U compo over the Tevez thing). You get it now where if you've been relegated anyway a late season points penalty is rolled over to the following season, don't see why you couldn't have the reverse situation apply. Of course it's better to close loopholes, but it's better to get a set of rules with loopholes in place to take out a lot of the problems rather than leaving it as it is while we spend years arguing over how to close every single one to create a perfect set of rules. The situation you're describing is a club self-destructing after a specific set of events. That is the concern of the club itself, and is a secondary issue where the footballing authorities may be acting outside of company law if they try to restrict it, it would certainly be much more open to challenge in court. The rules being introduced are intended to protect other clubs from the actions of one club. Remove the gain from doing it, and one club won't feel the need to do it just because otherwise they'll be disadvantaged by another club doing it. Stop Fulham spending a truck load of money they don't have by making it pointless and all those around them can spend sensibly without losing out on the pitch.
Football clubs needs to be protected from the owners rather than other clubs, see Hearts, Rangers, QPR, Portsmouth etc. The owners should not come out of it with all their money back while the club ends up bankrupt. Both things would be solved with a salary cap, cut their wages so the players can only get x% of revenue. All these problems were the result of Bosman, quite ironic that he is now living off benefits.
How many times, the ability to protect the clubs from the owners may be outside the legal ability of the football authorities. Rather than spending years and years going through the courts during which time every club is exposed to the risk of their direct competitors being run irresponsibly they're introducing rules that make being irresponsibly run completely pointless in all but a small number of situations (ie avoiding relegation for a season). Of the 4 clubs you've mentioned at least 3 of them encountered the problems because they were pursuing trophies or European places, so had the rules been in place wouldn't have gone that way. How is restricting wages to a % of revenue better than restricting total expenditure to a % of revenue though? That's like saying banks restricting mortgage payments to 40% of your income is better than them looking at everything you spend and restricting your total expenditure to 100% of your income, what happens if you're spending 80% of your income on paying other contracts?. If you set the cap on one element of expenses you can still go and overspend on everything else, so set the cap on total expenditure. It also stops them being able to pass off player wages as other expenses. I can immediately see players having an increased signing on fee or deferred wages that are withheld by the club incurring interest due to the player (topping up the wages). The interest would then be claimable as a finance cost rather than wages, and at the end of the season the club pays the wages. Providing the club was free to settle the balance whenever they wanted, meaning it wasn't an income the contract guaranteed the player I can't see a problem with it from the accounting side.