We had a situation where we wanted our current trailer and couldn't buy it right at the time that was most convenient. We had to wait. One week before our first trip in May of 2013 we were finally in a position to do it. We went, looked, bought the week before. We did the PDI and delivery the day before the trip. Got it home and had to load it.
While we love the trailer and are not sorry we bought it, in hindsight we should have waited until after that trip. It was a stressful week that should have been a lot more fun. Had we waited we probably would have gotten a better price, and had more time to breath. And we were not in a situation of being upside down, no way I would have done it then.