You seem to have a lot of questions here Swedie, so let me do my best to find some of the answers for you;
Yes they could have borrowed from the bank, how much, we do not know. Whether or not it's peanuts is relative to each person. And when you say they borrowed for tools and payroll, do you mean average employees like janitors and secretaries or do you mean the big salaries guys like AS were paid (dispute obviously not fulfilling his duties)? Are you also claiming that DM having no patience or ambition is what caused WM to kill himself, or that it was the business going 'belly up' (although again, I am not sure we have verification of that)? I personally know a lot of people with lazy, no good kids who are not in anyway suicidal or in fear for their lives, and many businesses that go under without the owners dying.
It is my opinion that DM has held other jobs or owned other companies prior to becoming CEO of his family's company, he did after all try other interests like cooking. It would not be so unreasonable to assume he earned a living despite being born into a comfortable family.
As was pointed out earlier, all real estate transactions require a financial check by their lawyer or real estate agent to track where the money is coming from, so it must be assumed that the properties that he bought were bought properly, using funds from an acceptable source.
I believe the tools DM was trying to sell were advertised for sale after the death of WM, and after the cancelling of the MTO certificate, although if any sold, we are not yet privy to that information. If he had borrowed large amounts of money for his business and instead put it into real estate, the bank would have noticed, this isn't a student loan, they keep a close on on the money that they lend to businesses. And if WM had given money to DM to purchase the farmland, it wouldn't have been because he knew he was going to die in a few more years, in my opinion, and if it was, what of it? Same if he gave him a gift of money to build a house, or not, what does that have to do with anything relevant here, I wonder?
If AS's account is taken word for word as the gospel, than so should the real estate agent's word that he was a nice guy buying a property who happened to bring his father along one time. In which case we should also take DP's word for it when he said DM is fine financially (so maybe not in debt to Revenue Canada or a bank) until we see proof to the contrary, otherwise we are just speculating without even circumstantial evidence to back it up, in my opinion. To me it is a waste if time speculating if he overpaid for the land, since he picked the price he paid, and the sellers afterward had felt it was worth more.
Why shouldn't he buy a condo when he owned a vacant farmland, it was obviously an investment, and whether or not he got offers for his properties before his arrest is rather moot, is it not? And generally people who are flat broke cannot purchase properties, either to hide their money (what money, they're broke?) or to turn into investment properties, banks don't lend to broke people. Whatever his relationship with his mother at the time, why would he need to put those properties into his mother's name before his arrest, why are we assuming he had to hide that he didn't feel he had to hide, I wonder?
To me, DM seemed completely reasonable in his dealing with AS that was reported, I would have asked the same questions and also would have wondered why the man hired to do his job still hadn't done his job. I think asking AS to discuss it over dinner when things got heated shows a foresight and self control that in my opinion AS did not possess, or he would have suggested it himself. I think anyone would have been apprehensive about pouring more money into something that had no returns as yet on the horizon.
And, I think someone else has already pointed out, that Waterloo invested in the airport because the are also benefitting from those improvements. <modsnip>.
