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Single sled deck or open trailer

I have an '07 2500 HD Crewcab with Longbox. The deal is, I also have a 36" deep dawg box that pretty much stays on the rig year round (and all hunting season). I'm trying to determine which would be easiest for hauling my '07 M8 (162"). If I pull the dawg box, the track itslef barely sticks out past the tailgate. There's no way it'll go with the skis hitting the front of the dawg box. I have the dawg box on a pedestal that raises it even with the wheel wells, so I can still fit lumber, etc underneath it, but I could raise it about 8 more inches to fit the ski handles under it too. That would give me about 11" from the tip of the skis to the nose of the sled, but that still leaves quite a bit of the track hanging off the tailgate.

I'm thinking of getting on of the pivoting ramp-style sled decks and rigging it up so it only goes as far as under the dawg box, and then the whole sled is sitting on the ramp sticking out past the tailgate. But when I have no sled, I'd want the ramp to be easily removed or slide all the way under the dawg box so I can close the tailgate. Seen one for $600 out here in WA.

Or, I've seen several two place open trailers for $1k or less on craigslist.

The sled stays in the garage, so the whole off season, a trailer would be taking up space at the house. Plus, wouldn't it be easier to turn around and what-not without a trailer. I'm brand new to this and doubt I'll be hauling anyone elses rig around, so it doesn't really make sense for a trailer (other than loading and unloading being way easier.

The guy I bought the sled from gave me his 7'6" ramp, but the thing is just no fun loading into teh bed with the short ramp. So at a minimum, I'll need a longer ramp (assuming I just leave most of the track hanging past the tailgate).
Any ideas?
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I would go with a two place trailer. The if you want to go riding with a buddy sometime you can just throw both sleds on the trailer. Plus the loading and unloading is much easier. just my .02
 
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