Im not in such a bad, or odd position, but I will say that getting time to document really isnt always on the to-do list at places. I was a work study student for a small community college (2000 students, 900 pcs, several server) and the admin had almost zero documentation because he never had time to do it between managing accounts, server and telephone issues.
Then i interned at a large health system. Some stuff is relatively well documented, some stuff has a little to go on, some stuff has zero and you cant even find who worked on it last. They are asked to document things, but they arent always allotted time.
I work for an IT consulting company now who services over 200 customers in eastern north carolina. In a given day I might go to 4 different customer sites. I try to document while Im on site, but then I have to clean that up, put it in the notes/visio that the company uses because another tech might go to that site in the very near future, and get that uploaded to the office so someone can get it.
It's tough, and while the techs generally do a good job of it, stuff gets missed because we NEVER get administrative time scheduled to do documentation.