Advice on Booking Business Class Tickets with Amex Points + Cash

Hi all, looking for some advice on booking business class flights with points & cash.

Context: My fiancée and I are getting married in Italy in mid September 2024. We're looking to try and book one business class flight from Vancouver to Italy, and book the second ticket with cash. We are ideally looking to fly into Florence, but also open to flying into other cities – especially if we find a better deal (points or cash).

We currently have 300k Amex (Canada) points, which we're thinking of transferring to Aeroplan points 1:1 and booking through Aeroplan. The current pricing for a one way flight is around 250k points, or $3,500 CAD.

Questions:

• Is Aeroplan the best travel partner to convert our Amex points to? Are there other options we should consider?
• When is the best time to book? Are there downsides to waiting into next year? Aeroplan mentions there are x # of seats left – will the business class seats be fully booked up and result in us spending more points / cash?
• How do we know when we've found a good deal? Are the current rates (250k points / $3,500 CAD) average, low, or high? Are there 3rd party sites or apps that can help us monitor the point fluctuations? Or resources that show what is a good vs bad deal based on destination and time of year?
  • For additional context, we booked one way business class flights to Paris last year (April 2022) for around 50k Aeroplan points per ticket – which is significantly cheaper than what we're seeing now for flights to Florence/Rome/Milan. Not sure if this is simply due to supply & demand of travel last year vs next year.
• Anything else we should be aware of or consider?

Thanks in advance for the help! Really appreciate it.