One of the first things I started doing after learning how to edit in OSM was labeling all of the many apartment complexes and trailer parks around my city. I live in a rather poor city and a college town to boot, so there are more of these kinds of housing than would be typical. A common problem is that many of the commercial maps won't have these labeled at all, so when someone tells you they live in Such and Such trailer park, then it can often be pretty hard to find.
I've found a (to my very best knowledge) public domain plat map of my city. This is an online version of all the records that are public access in the city archives. Besides the owners, it also lists the original subdivision, which led me to marking the subdivision name in the name field of landuse:residential. That is, until I came to an older part of town where many of the houses have clearly been torn down and rebuilt several times since the originals. There I'm left with some rather odd names that have little to no relationship to what people actually call the place. I've come to a compromise between practicality and historical correctness. I'm including the name as old_name so that the information is still there, but doesn't claim to be the common and current name. In the event that I'm wrong (after all, I've not yet been living in this city a year), then it would be easy enough for a later user to change it to the name field and carry on.
Meanwhile, I'm still happily marking out the jigsaw puzzle that are the subdivisions in the old part of the city. It has been fascinating work as I can now see why a group of houses look alike or why the streets are laid out in neat rows then suddenly a curly squiggle as the subdivision changes.
The only thing that bugs me is sometimes there are little holes in the swath of landuse:residential between the subdivisions where two sides of a street belong to different subdivisions. I've seen the method of attaching the nodes to the street itself, but I just don't care for that method. I won't change what someone else has done, but it's just not my preference. I suppose I'll just have to be reconciled to funky little holes. Ah well, they don't show up except at a close zoom anyhow. Most of the time.