It can go both ways. The 100 nights/flights person gets really familiar/routined to what's on offer and is going to complain when you change the brand of rum. Corporate expects you to personally welcome them, read their preference notes and make sure you give them something to bring to their kids because it's their birthday.
You're expected to upgrade them to the best available room/seat but they complain to corporate when someone that does 101/year gets the upgrade instead. If their flight gets cancelled/delayed because they flew into a known hurricane, you better watch out for it and proactively re-book them or hand out food/hotel vouchers.
The $5 discount OTA person... give them the crap room/seat that nobody else wants and just ignore their whining.
Just based on my experience of being the latter and trolling flyertalk...
You're expected to upgrade them to the best available room/seat but they complain to corporate when someone that does 101/year gets the upgrade instead. If their flight gets cancelled/delayed because they flew into a known hurricane, you better watch out for it and proactively re-book them or hand out food/hotel vouchers.
The $5 discount OTA person... give them the crap room/seat that nobody else wants and just ignore their whining.
Just based on my experience of being the latter and trolling flyertalk...