Another thought - what's the gvwr on the trailer?
here in Manitoba, we need a minimum of a class III drivers license to hook on and tow a trailer at or over 10 000 gvw.

I don't know wha the equivalent of a class III license is were you are from, but for comparison sake, it's what we need to drive a tandem axle dump truck (air endorsement if air brake equipped as well).

 

Good luck.. I had an 02 1500 4WD quad cab shorty with a 4.7L with 3.55 gears and auto trans. Pulled a 25' bumper pull travel trailer loaded with water and gear and 4 of us in the pickup and atv and fuel and more gear in the bed of the truck. Overall weight loaded just on the travel trailer was 7200 pounds. Set up the truck with air bags, tuner, dual exhaust, and homemade cai. Pulled trailer 1 time over 200 miles one way with lots of hills and when we got back home, a new 19' fifth wheel was purchased and a b&w hitch installed plus a flatbed trailer in the rear of the fifth wheel to pull the four wheeler. Shaved about 2900 lbs. Traveled with the trailers hooked up twice and then sold the truck and bought a 2500 Hemi. Wow now it is like nothing is back there. Talk about spending a lot of money..........

 

The best suggestion I've heard over all who tried talking you from killing your 1500, risk harming others if things
break and go out of control because you have some nasty mountains and valleys to make. Hit the lows doing 80
and over the top maybe 10 mph, if lucky.

Is;
Rent/hire a tow service. They work those roads every day. Run a web search and start bidding. Check their credentials as you would any contractor. Preserve you sanity, you requested professional advice and what I've read thus far, you well received great stuff w/o costing a dime here. Enjoy the boat.

 

Most of you have provided good input. It's interesting comparing different opinions from online folks and local folks at our 4x4 center and from workers at the marina's. Truthfully, most experienced and knowledgable folks that I've spoken with feel that as long as I have air bags, tranny cooler, engine oil cooler, load D tires, good brakes on the trailer and drive safely that it won't be a problem for towing only a few trips a year. I laugh at the white-knuckle comments because that shows inexperience. If you tow safely, make corrections for sway using the correct method, and downshift going down hills, you shouldn't have any white-knuckle moments assumming everything is functioning properly. Since I've been towing 8k lbs for the past 8 yrs, I'm comfortable and safe towing heavy loads. Since the actual weight is between 9500-9800 lbs fully loaded, a CDL license isn't required. Like I said, some of the input here is good. All things considered however, I do think it's going to be quite a stress on my transmission and therefore have chosen to have the boat delivered to me. I'll make some serious upgrades to my truck before towing that much weight. I wouldn't want something to go wrong and end up hurting someone. The one white knuckle moment I had was when my old truck lost all power and stalled while I was towing 8k lbs down a steep, windy, mountain. I put it in neutral and tried to restart the engine, however couldn't. I pushed down on the brake with both feet and pulled back on the steering wheel and was able to stop it a mile later and pull it on the side of the road. I found the only burm capable of fitting my truck and trailer on that day. Amazing! Anyway, thank you all for the input and best of luck to you all!

 

No offense, but you say you are experienced at towing; yet you shift into neutral on a downgrade????? Again, not trying to start anything...just sayin'

 

HemiMoparGuy1981 - Strap your trailer on your truck, find a very steep hill and get your truck moving at around 40 mph. Now turn your truck completely off (which would simulate the complete shut-down that I experienced) and then try restarting your truck without placing it in neutral.

Ya know I’m finding that many people in this forum are egotistical, narcissistic, and most eager to bash on others to make themselves feel more superior as if it would improve upon their image to others. Truthfully, it makes them look childish and insecure. Enjoy your trucks. Peace Out!

 

Well, that's an egotistical, narcissistic thing to say and bashing on guys who tried to give you advice on how to keep your truck in one piece, NOT harm or injure yourself or anyone else and NOT lose your bank accounts or property when your insurance refused to cover you BECAUSE YOU'D BE BREAKING THE LAW.
You came on here seeking advice and when you didn't get the re-assuring answers you wanted to hear, you copped an attitude.

I was gonna give you a vacation from here, but on second thaught, I just really don't like your attitude in general. "PEACE OUT"!!!