SO boxes DO NOT hold their value.
Let's do some math:
New SO box - $2600
Est. value after a couple years - $1300 best case. (see CL)
Depreciation $1300
HF Box - $400
Est. value after a couple years - $100
Depreciation - $300
There are reasons to get the SO box but holding their value is not one of them.
I picked up a set of Snap-On 650/655 combo for 450 dollars in nice shape. It came with a HF side box. So so much for the resale value. I run across Snap-On and Other truck brands all the time for little to nothing. Easy credit is what sells Snap-On, MAC, Cornwell, Matco boxes. If it wasn't for that they would be a rare find. If everybody had to dig out all the cash at once most techs would own a Craftsman or HF box.
I have no idea where you get your resale values from. I had two of the HF boxes in my shop when closed it. I had 330 in each box. I had no problem getting 200 a peice for them and that was after 3 years of use and to a good friend that I cut a deal.
Just because you see a box on CL listed at 1300 doesn't mean thats whhat it sells for. I bought a MAC Tech 1000 that was listed on CL for 1200 dollars and took it home for 500. I sold it to one of my techs for 1000 dollars at 30 dollars a week from his check.
I have already sold the HF sidebox off the boxes I just got for 100 dollars to my son. They cost 199 new or 160 with a 20% coupon.
My Macsimizer takes up a lot of room in my garage, It's 96 inches long and 29 inches deep. Because I have retired I have given much consideration into downsizing my boxes because I don't need near as many tools, I now have 4 sets of tool boxes in my 26X32 garage. I asked a dealer how much he would be willing to spend to buy my Macsimizer. 2500 dollars which is less than 1/4 the value they cost new. he would sell them on credit for 5000 dollars. I just decided to keep them and look at them. It's not just about the % of what you paided but how much you lose in cash value. Even if you did manage to find someone to give you 1300 dollars for the box You lost 1300 dollars over 3 years. It cost you 325 dollars per year to store your tools. With the HF box if you paid 350 for it and used it for 3 years and you sold it for 100 dollars(you would have people beating down your door at that price) you paid 250 dollar to store your tools over three years at 83 dollars per year. Realisticly you could get 200 for a used HF 41 inch box easier that 1300 for the used Snap-On in a cash sale. That would be 50 dollars per year.
Despite the fact that HF boxes are imported and the others are made in the US you do the economy more good by spending your money in other places than the tool truck. For what the payment cost on a nice mega dollar tool box you can buy a new American built truck. That keeps a lot more Americans in a job buying tires, oil filters, service department, dealerships, aftermarket parts, brake pads, etc than just the tool man and box builder. While I enjoy having a nice box and Ive already been down this road from floor sweeper to garage owner and everything inbetween I know the one plce that I've really screwed up was buying tool boxes every year or two. I've been making payment to tool men longer than morgage companies.
Maybe just maybe the influx of nice toolboxes out of Asia will drive down the price of toolboxes from the Big 4. The big 4 have gotten out of control on tool box prices. I think they need to be knocked off their pedestal and put into the real world. No tool box is worth 30,000 dollars but they are getting common.