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What’s an upgrade? Titanium/platinum status for years and have gotten less than 5. :)
Sometimes they might not be obvious. Could be a higher floor, corner room, better view, etc. Other times could be a suite or bigger room. Depends on a lot of factors and is probably more difficult on weekday business travel. Never hurts to ask though as it is something you’re entitled to pending availability and some other specific terms of the program
I’ve seen people have success with messaging the hotel through the app once checked in and asking about upgrades
Rate seems to play a factor too
Combination of factors, including status and timing. Honestly, getting to know the desk staff is most effective. I had a five month stretch at the Saint Regis property, where my upgrade rate was 80%. And most of those to a true one bedroom i.e. with second bathroom in separate living room. I knew every doorman, front desk person, and bartender by name