Originally Posted by scubaccr

Agreed, mixing entry level free night (award/CC night) with much higher room cat , leading to free night being a suite is poor use of award night , and only likely to work if many paid nights alongside a single free night.

I see the pre-arrival high upsell (bad value for free night if you are the guest) as being priced that way as the IC will be taking the high cat room out of sale inventory for your award/CC free night that might otherwise been sold.

If OP doesn't bite that high pre-arrival upsel offer, and at checkin the IC has still unsold suites the second night, then typically hotel upsell offered is 20-35%% off the delta rate difference (booked flex room to flex of suite).
There is also a smaller chance at checkin the IC may let it go if guest refuses as hotels really do prefer not to move a guest betwween rooms, though as lowly Ambassador guest won't get foc lounge on free night unlike on the first paid night if included in Studio/J-S Suite rate.

More likely to go well and foc for Guest, if guest suggests they get the J/S (Studio suite) both nights, forgoing Amb 1cat upgrade on first paid night to have foc multi-cat upgrade to paid room cat on the CC/award second night.