I've got an unusual situation.
Living in a high rise condo I've haven't tipped the office staff, security staff, maintenance staff, gardeners, etc. etc.
I realize if I lived in New York extortionate tips would be required for door people at least. But this isn't New York.
I kind of wish the condo management organized a formal tipping jar for New Years that would be shared with all staff in which case I would throw something in, but they haven't.
I have tipped maintenance staff when they do a service for me in my condo at the time of service, but that's different.
Well now I have one specific door/security staff person that has consistently given me ridiculously good service over a long period of time. From little touches to somewhat bigger things. I don't really need anything that he's done, but it's really been charming and I certainly wouldn't be so rude as to tell him to stop it.
One example of how unusual this is. If I'm loaded holding shopping he enters the elevator and pushes my floor. It goes on and on. It's a little bit of entertainment to see what uncalled for service he will do next.
So obviously he well deserves tipping. But it gets tricky. Do I tip a little bit for every little thing or do I give him a very big tip for the New Year? If I only tip him and no other service staff isn't that kind of rude? I'm also a tiny bit concerned that it would "corrupt" the situation as I really don't know if he's some kind of freak that just loves doing that sort of thing and it would be insulting to tip suggesting he was doing it for that. He keeps doing it, never hints in any way that I should tip, and I don't expect he would stop if I never tipped.
Not sure at this point.