Don't think you transmission will hold together because you transmission is rated at 2000 lbs. and you are pulling 2000 lbs. Getting the trailer up the ramp can exceed max tow capacity. In fact, if you have a Dodge Caravan the transmission will crap out just trying to run the van down the road. That said there are lots of good 16 foot boats with trailers that should fall in the 1200 lbs. range. There are also vehicles with good transmissions that hold together, some of the Ford truck series come to mind. Do a Google lookup on your transmission/vehicle, you'll get a world if info. Yes, I do have a couple Dodge Caravans, use it to pull a 12' aluminum boat so the crap transmission is not really a factor in that regard.
I'm guessing a Subaru?!
If you have something with 4 wheel low option, that would be great for up the ramp. That would help with any concerns of pulling up the ramp. If it's 4wd (as opposed to Awd)remember to try to only drive straight, that extra weight and dry pavement can cause problems with 4wd.
What ever your concern don't forget STOPPING. It's not hard to wire in an electric brake controller.
If you don't have a hitch yet, try and check to see if there's a higher class hitch (class II or better yet class III). Not suggesting that you tow more then your rated for, but the higher class has a higher rating for tongue weight, just in case your 'load' is not balanced correctly.