Yeah I'm trying to get the 50% or as close as I can on most stuff
For general hand tools that's probably what I'd start off asking, but take less if offered. I suspect with a 25k tool box you're going to have to take a lot bigger loss than 50%.
The problem with big ticket items such as a $25k tool box is if it's 25k in the Snap On catalog a dealer will probably realistically sell it for $12-15k after rebates, promotions, etc. Most people buying these boxes can't afford to shell out anywhere near that for a tool box, but they are able to buy it off of the SO truck with a trade in and SO financing. Since they can't pay cash for it, that eliminates 90% of the people that want that box from being able to buy it from you.
The people actually have the money and desire to buy it will usually know that you can't sell it (and that they won't be able to either) and they don't want to pay a reasonable value for it because of that. The internet is full of expensive used SO tool boxes for $2-3k that just don't don't sell.
In fact, the majority of mechanics I know can't buy used tools because they can't afford the tools outright. Almost all of them have huge amounts outstanding on their credit account and they are forced to buy new off of the truck so that they can finance it. Used SO also doesn't have any warranty so that eliminates a lot of interest as well. Overall, it just makes selling tools for anywhere near what you have into them impossible.
As said, Mac and Matco don't really hold their value at all. They are way worse than SO when trying to sell them. For example the last auction I went to sold some Matco wrenches that looked new for $45. I looked them up on the Matco website and they were over $300 new. Mac tools were going for similar prices. Snap On does better, but they still don't bring a lot of money on the secondary market.
