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Depends on the hotel and occasion.
Wife and I going to visit friends in a random city? Cheapest room.
Honeymoon in the Maldives? You bet I paid the upgraded prices for the overwater sunset at the St Regis
How much are those upgrades prices? 😬
Chief
Upgrades are so hit or miss (mainly miss since bonvoy), I reserve the room I want.
I always get the cheapest room and get upgraded to the best room in the building. Ambassador status
Chief
Depends on the situation. If it’s just me, just work, or a one-off kid thing (like staying somewhere for a sports tournament), I book the basic room and see what happens.
If it’s a family vacation, I book the room I want.
Pro
I’ve done it, but the upgrades happen less than you would expect so not a great strategy unless you’re fine with the cheaper room. And I’m ambassador.
Upgrades at Marriott? Good luck.
I try to be in the hotel room as little as possible, it's just for sleeping for me. The beds are the same, so I go basic room and sometimes get an upgrade.
As platinum elite, I generally assume I will get upgraded if they have it available, so it matters more if I think those rooms will be available when I get there or not. Holiday weekend in Miami is going to be different than a random week in Vegas
Pro
I almost always get upgraded. And also rarely to never spend actual money on a room unless it’s being covered by someone. Between cards, endless points etc, spending money on any hotel room for personal travel is often unnecessary. Would guess it’s similar for other titanium elite lifetime folks.
How much time do you plan to spend in the hotel room? Resort stay? Pay for better room. Stay where you will be exploring? Cheaper room.
Yeah almost always go for cheapest room