Your GVWR is approximately 7200, just a rough calculation of your towing habits shows you to be right around 7000 if you assume 10% trailer tongue weight. Your GCWR is roughly 11,300 and you're at 17,300 approximately. With the bags I'm sure it helps, but my concern would be liability if something went wrong. I doubt your insurance company would cover you if you (or anybody) exceeded your towing capacities which would leave you open to law suits which I personally want no part of. The litigious nature of this country is absurd and I've alway made sure I'm within my bounds when towing. Also think about panic stops or accident avoidance maneuvers, trailer tire blow-out, bearing failure, etc. and you're into another league, also personal liability for injury to another party.

If you only do it a few times a year for local jaunts it's just dice rolling. Regarding the OP pulling a boat a couple thousand miles is just looking for trouble.

I did not calculate the breastssssssessess in there, if they'll be present then just ignore all the above and purchase a Freightliner :D

I get worried towing my Mini Hawk behind my F-350 dually--only because I can't even SEE it when towing! That's why I bought the Tahoe! :D

f-150
 

around town to a gas station o-k but not to Fla. I know from experience i have a 35 lightning and i am using an f-150 to move it around locally, would not even think about going out on and interstate with it on a long run. Looking for an F-250 diesel right now.

The bottom line is if the truck, trailer, and hitch are rated to pull the weight, your fine. This assumes you have proper setup and knowledge of how to tow. I see my fare share of idiots with very capable trucks 3/4 ton and 1 ton rigs pulling too fast, trailing to close behind others, and doing stupid things. No matter what rig you have if your set-up sucks, and you are foolish with your driving, its not safe. If its rated for it, your good.