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I have my doubts about that rack and your bedsides holding the weight of all of that long term.
We run racks on all our pickups, and we always building them ourselves and tie them clear down to the bed of the truck, not just the bedsides. The bedsides will crack with rattles of going down the road. Plus with the trailer you are looking at being pretty damn tall too...
Oh, and unless you and your buddy both are nicknamed Mongo, I doubt you will be lifting 250lbs up over your head onto that rack. Again, thats a lot up high, it won't be fun to get up there, and then it will really suck getting down.
Again, we use racks all the time, and loading and unloading stuff that high up isn't as easy as just picking it up. Its a damn good way for two guys to end up with a very nice back injury.
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