We will be traveling from Boston to Australia on United in December 2023 as a family of four. We have the requisite 240,000 points to request upgrades (+ fee) from coach, but will need to transfer in points from Chase to do so. I have Silver status on United. No upgrades are currently available, but we can go on the waitlist. Is there any advantage to paying the fee and moving the miles in now as opposed to waiting until say 1-2 months before the flights? Does getting on the waitlist earlier increase our chances of the actually getting the seats? Also, if we pay for Premium Plus are we any more likely to get off of waitlist for Polaris?

Thank you for any insights.