Alright, was hoping I could get some opinions on this.

I have a 2006 Grand Caravan (6 cyl). It does have a hitch on it but does NOT have a towing package. I used to use it to tow my jon around in a crunch(it weighed maybe 500lbs at most).

The standard maximum towing capacity on the van is 2,000 lbs. The boat I have is rated at about 1,002 lbs with the trailer.

I have no intention of using the van all the time but in a crunch, how safe would say periodically using the van to tow (maybe 45 minute drive at most), would be for the tranny?

I have no intention of getting on the highway with it or going long haul (got a truck for that). My main thought is a campground about 45 minutes from here. I use the truck to tow the camper, if possible would love to have the van tow the boat when we go so I do not need to make 2 trips but I do not want to go replacing a tranny either.

Thoughts? Opinions? Am I crazy to even consider it?

Will the van stop the van, trailer, and boat in safe distance.  I would think that would be the deciding point.

It will. I would not be happy about it but it would stop it quickly. The one thing i can say about that van, it's breaks are good.