I need to pull a boat in the summer, about 8k lbs (boat and trailer) plus I'll have a several hundred lbs of equipment in the truck. I am planning on traveling around the Great Lakes sometimes pretty long distances. I think I want to go with diesel. I am looking for suggestions as to what truck I should consider and why. I've looked at Fords, Chevys, and GMCs so far. Any ideas are welcomed! Thank you.

 

The entire Super Duty F-Series trucks are the towing powerhouses for me.
The F-350 and F-450 are the kings of the Ford towing fleet.
It will absolutely be perfect if you're planning to tow your bout around towns.

 

Aside from brand and model of truck, you may want to consider putting a leveling kit on your future rig to prevent rear end sag while hauling your boat.

 

I think you can look at a Ford F-150. It has good tow power for your trailer and bikes. It also handles snow and cold weather well. A Ranger can work too, but the F-150 gives you more space and more pull. The Dakota can tow, but parts can cost more in some places.
Since you want an older truck, try to find one with a clean service record. Check the frame for rust. Make sure the brakes, tires, and tow setup are in good shape. A V6 can pull your load, but a V8 will do it with less strain if you change your mind later.
You can also check marketplaces that use Live Video Streaming™ so you can see the truck in real time before you go look at it.
Hope this helps.

 

You can go with several brands, but if you want one truck that works now and later, I say go with Ford F-450.