Originally Posted by
kisis
1. Do I just purchase the Premium Plus tickets (without the $ and miles upgrade) and see what the offer from United would be to purchase an upgrade to business tickets? Is there a chance it would be less than buying the business tickets outright? When would I see an offer to pay to upgrade to business?
Sure, you can do that. You’d see a cash upgrade offer as early as checkout, and that offer may change (up or down) at any time. If you waitlist for the mileage upgrade award, the cash upgrade price is likely to disappear, however.
Originally Posted by
kisis
2. If I do just purchase the Premium Plus tickets to see what the business upgrade amount would be, and it's more than I want to spend, do I still have the option of doing the $425+20k miles to upgrade? (I know I would be on a waiting list). Is that something I could add on, online or would I have to call a United agent?
Yes, you can still waitlist, and can do so online. I recommend this approach over trying to use the Advanced Search flow.
Originally Posted by
kisis
3. If I go with the Premium Plus tickets with the $ and miles upgrade, what are my odds of getting upgraded, given there's a waitlist (but I will have Premium Plus tickets and it's low-season)?
Based on the inventory numbers, your chances on the outbound are excellent. The return is a little more constrained.
Originally Posted by
kisis
4. Is there a better way of doing this, that I haven't considered?
Perhaps. The outbound leg currently has available upgrade inventory for Premium Plus. You can save about $300 per person by buying economy outbound, premium economy return, and then applying your upgrades. On the outbound, you should have the option to confirm Premium Plus and remain waitlisted for Polaris. If the Polaris upgrade doesn’t clear, UA will keep the miles but refund the co-pay. The only downside here is that you will be lower on the upgrade list, The upgrade list is ordered first by passengers using an upgrade instrument from a Global Services (invitation-only top status tier) account, then by cabin, and then by status. So with a Premium Plus ticket, you’d be ahead of any 1K, Platinum, Gold, or Silver member in the economy cabin who is trying to upgrade*, but with an economy ticket, you’d be behind those people. Since the list can change — a higher status passenger who buys a ticket later will still have priority over a lower status passenger who bought earlier — there’s no way to know whether or not this will have a material affect upon your upgrade chances.
* unless they’ve had a GS friend / family member apply for the upgrade on their behalf, in which case you’d be behind them either way.