A Donation button could be placed in a custom block on the sidebar for convenience.
Winnie could create a Paypal Money Pool (if that's available in Canada) on his account.
"Money Pools are an easy and fast way to collect money with friends. Whether you need to raise money for a holiday, a group gift, or for regular shared expenses, just create a Money Pool and share it with your friends and family. Please note that you’re responsible for spending the money collected for the purpose set out in your Money Pools page. Your friends can chip in in seconds. If they don’t have a PayPal account, they can set up one in minutes "