I have just engaged in that most ancient of New York City Holiday Traditions - the distribution of holiday tips for the door staff. This is a time-consuming and delicate dance of envelopes, diplomacy, and hard cold cash.

For many, it is a time and a task fraught with worry and concern. But never fear. A fear shared is a fear halved. Or something like that. I have been tipping my door staff for 16 years and this is what I have found people worry about most often:

1. Who gets how much?
2. Does the newest porter get the same of the porter of long standing?
3. What about the doorman who really went out of his way when there was a leak in the air-conditioners on a Sunday afternoon and nary a repairman could be contacted?
4. Do they compare envelopes?
5. Who gets the most?

Answers in order in the Greater Gothamverse -

1. That’s up to you. It’s very much something to be decided on a case-by- case basis. Where you live, how many are on staff, what they do, and how big a building you live in can all come into play when making this call. Typical advice ranges from $25 (it’s a small building or you just moved in, etc.) -$100 (it’s a huge building and takes ages for the porters to gather and get rid of the garbage each day, the porters walk your dog, etc.)
2. Excepting unusual circumstances (the porter who walks your dog can get something more than the ones who don’t), everyone in the same position gets the same amount.
3. If someone really went above and beyond during the year - helped you in aforementioned leak situation, do your grocery shopping when you come down with chicken pox, found you a fantastic new house cleaner. They get extra.
4. You bet they do.
5. In my case, it’s the handyman. I have an outstanding handyman who now only can fix anything but whose workroom downstairs contains any part needed by any appliance you can name. He is a fix-it god and given top rewards accordingly. This also ensures that he fixes my stuff first during the year. Still, in most buildings there is also a super.Assuming they are not one and the same (they are not in my building), no one gets more than the super and/or the building handyman. No one. Not even the one you may (or may not) be having the affair with. After all, he’s getting something extra already. (Oh come on - We all know it’s happening. I personally think it’s more East Side than West Side but that’s a guess.)

Stick to cash. They don’t want the free CDs your music company produces. They don’t want an Amazon gift certificate. They don’t want some cheap piece of cotton that says “My Residents Went to Cancun and All I Got Was This Lousy T-shirt.”

And please, don’t give them liquor. Someone in my building did that one year - gave each guy on staff (all 21 of them) their own bottle of very good whiskey. Generous, right? Yes, buy problematic as well. Two of the guys were devout Muslim and didn’t drink (so they gave their bottles to the evening doorman). Two were equally devout, non-drinking Catholics (score two more for the evening doorman) and three guys were recovering alcoholics (and three more for the evening doorman). The evening doorman, it must be said, was both well watered and flush with last minute gifts for his own friends and family.

I’ve distributed my envelopes already - having found some generic “happy holiday” cash envelopes at the office supply store. I always try for the generic “happy holiday” in silver tones with blank interiors rather than something covered in candy canes, cutesy cartoons or dripping with earnest and solemn statements about peace for all mankind. After all, not everyone in my staff awaits the jolly fat man in red, sees all of mankind the same way or has a preferred spelling of Channukah. “Happy Holidays” is quick, non-committal and you don’t have to buy more than one kind.

If you’re still not quite sure what to do, do not despair. Every year, this topic gets more media coverage than many actual news stories. You’re bound to find some helpful advice out there.Curbed posted a memo back in 2005 that had been sent out by a management company to the residents of a building with the management companies “suggestions. The comments alone (125 of them) are worth a read. Then Curbed posted it again in 2006 just for old times sake and because as a subject in Gotham it never gets old.

Holiday tipping isn’t just for doormen though. New York Magazine did a poll on the subject of holiday tipping in general. The poll was done last year and while the amounts can only have gone up, I imagine they haven’t gone up all that much. Emily Post, who has answers for everything - even things you didn’t know you needed to know - also offers some advice (updated for 2007) for all sorts of holiday tipping from the doormen to the manicurist to the mailman.

Bottom line: you are the one on the spot. You know if they helped you out or whether they avoided your eye. Don’t worry about what your neighbors give (in my building, what my neighbors give is more an indication that they want to show off than anything else) and focus on what and how these people perform their job to your satisfaction.