Originally Posted by Often1

If by travel agent you mean a business with which you regularly deal and where you have specific contacts in your location, that may be fine. Anything else other than the air carrier itself is a problem in IRROPS or rescheduling difficulties. This is especially true during the pandemic because there are reduced schedules and there may be fewer options as well as travel restrictions for certain routings.

Separate tickets are also a significant risk, more so during pandemic scheduling and restrictions. If you are stuck in Hawaii for 2-3 days during high season, those costs may be much greater than your tickets.

Best to look for nonstop and single carrier routings on single tickets which are fully refundable. Nobody here can predict what travel will look like more than 30 days from now and thus anything you book for December is the distant future and thus, purely notional.

Finally, your booking strategy also needs to take into account your return strategy. As you are planning a roughly 60-day trip, if circumstances change while you are in Canada, you may need to change your trip to get back to Australia if the situation worsens or risk being stuck in Canada for a lengthy period of time.