I agree, the lack of tooling will fall into 2-groups. The person who is upgrading his machine and has use of the old tooling and the reseller who is trying to make the most profit he can.
When I bought my mill, I saw it on a craigs list ad with a asking price in the mid $4,000. It wasn't in my budget so I didn't even call the "surplus machine dealer". About a year later it pops back on at $2,700. I go and look at the machine, it is a VanNorman 22l stuffed in the middle of all kinds of machines; no tooling. I gave the guy my card and told him to call me when he is serious about selling.
In the mean time I drive by the place every couple of months just to see what else they have. When looking around I found a tool cabinet with all of the Van Norman tooling, A and B arbor support, (when these go on ebay they sell for $400+) 4-(horizontal) arbors, a bunch of NMTB 50 end mill holders, 3 (empty) shell mill holders and 1-8", 1-3" and 1-2-1/2" mounted face mills. Plus a bunch of miscellaneous stuff. I offered $800 for the mill, cabinet and all tooling. It was countered at $2,300 and I left. Over the next many months I'd stop in to look around and pull out my $800 for the mill and tooling. He finally said he would do $1,800 so I asked to see it running. The mill was pulled out of the middle of a mess of equipment and a fellow wired it up (3-phase). He started it, spindle went OK (better than expected ) but the feeds wouldn't work, they had a loud clacking noise. He goes to talk to the boss, I go and talk to the boss, we settle on $900 and $100 delivery. Wired it up to my RPC and the feeds work fine, looked in the manuals (yes, all manuals were in the cabinet) and it describes the feed noise, and states that the feed motor is running backwards and to recheck the connections.
When buying used machines, you have to buy when the deal comes along but that doesn't mean to accept the sellers offering. If it is a home shop person look around for suitable tooling and be firm but not unreasonable. If it's a reseller like in my case, the seller didn't have a clue that he bought the cabinet full of tooling that went with the mill, it was just part of a large lot that he got at an auction. Look around, you never know what you will find.
Sometimes to get the deal, you can't be in a hurry and be willing to loose the purchase, to someone else who values the equipment more than you do.
Mike