Last trip, I ordered just outside of two weeks. Disney Shopping said it takes them 7-10 days to get to WDW hotels. Sometimes longer, if there is a backorder or the order is large for picking/packing...
The WDW Resort hotels are really good with holds (although yes, they have been known to lose or misplace from time to time). Offsite hotels, I'm not entirely sure...
There is a list on the DIS of all the WDW Resort mailing addresses and how to properly address your package for shipping. I've got a toddler dancing around me, so I don't have time to search and post right now!!