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I had a setup like that one time to haul an 8 wheel argo, it was a bit high for weight, but it was also on a half ton. Worked well though, and really, when you are talking 4-800 lbs with a total mass of 5-7000 lbs (for our trucks) it's a small effect on things overall.
Grinder and crowbar? If you want a portable Fort Knox maybe you could buy a used armoured car. Lets face it, nothing keeps the smart guys out that want in bad enough, but not knowing what is or isn't in there will keep many out. Most items stolen from vehicles are smash and grab, or opportunities of the moment. (Things like CD's, change, wallets, etc, left in unlocked vehicles.) If they were smart enough to bring a grinder and crowbar, chances are they would just steal the whole vehicle instead, and open the rear at their convenience anyway.
The important part of it is if it is 'secured' as a contractor one should have insurance on tools etc to cover them where ever they are, jobsite, vehicle, whatever. The important part of that is they have to generally be 'reasonably secured'. Job box, locked vehicle, locked trailer, hard tonneau cover would all fit that bill.
People never seal my tools...they just see my tools and use them without asking.....if someone ever tried to steal my tools they had better run pretty damn fast.
never forget the one time I was sittin on the stoop with one of my city friends, when he saw that jag park there he grinned at me and said "watch this for a bit" sure enough about ten minutes later a white van rolls up and two guys junp out with air tools, that pair would have made a good indy pit crew
Depending on what you normally carry that might be a good deal.
1600 pounds on the deck, 500 pounds on the ladder rack both sound a little low to me.
When I was building houses, 3 or 4 ladders, a couple sets of pump jack poles and walk boards, 500 pounds would not be enough.
Unloading everything to haul something tall, would also be a pain as well.
In the end, if I stayed in the home building business, a job tool trailer looked like the best option to me.
Get to the jobsite, unhook the trailer and you had an empty truck to run for parts in.
At night, put everything back in the trailer and the tools leave with you.