Assuming David and his family are point-rich, using their own points to make their customers whole is similar to using their cash savings. I don't think either renters or David care whether new rentals are set up with David's cash or David's future points. It would be great if David is willing to put his personal assets on the line to make his customers whole.
There is indeed a point limit set by Disney, a member can only amass 8,000
DVC points, with a maximum of 4,000 points at any one resort.
Moving cash to different accounts is not as easy as it sounds. I would think in bankruptcy court the judge would ask for the financial transactions of the business. Also, although David operates his rental empire as a sole proprietorship, I would think he set up business bank accounts to handle business transactions. He could of course declare a dividend and transfer funds to his personal accounts, but because of the sole proprietorship nature of his business, he may still need to surrender some of his assets to his creditors. A judge would not look kindly on a business owner that declared a large dividend just before his business went bankrupt.
Now, you may wonder who those creditors would be, since renters and owners are unlikely to file small claims in Ontario? It would be the very banks holding his business accounts, who are now pressured by credit card chargebacks.
As an interesting fact - I chose to send David a refund for one of my canceled reservations, because I was able to transfer those points to someone else within days from when they became available. His team advised me to return the 70% via PayPal to a different account than the one who paid me originally. Since they gave me the instructions in writing I don't worry too much about not fulfilling my contract, but it is a red flag which may indicate that some of his accounts, either PayPal or bank, may already be in withholding.