How much would you pay for this box of end mills

Good buy! Sounds like you got your money's worth, and then some.
Those last reamers are curious. Definitely not chamber reamers (which are almost always (always?) straight-fluted), but also not taper reamers, which is what I thought before looking harder. Perhaps custom?

GsT
The hand-etched part number smells custom enough. I wonder what they would have been used for.
 
A quick search on Amazon for "end mill assortment" show about $17 for 10 pieces of Chinese HSS, guaranteed to last a least one cut through soft pine. (That's not actually true. There is no such guarantee).
I have said Chinese Amazon HSS endmills and I think you're not being quite fair. I used one to cut a 6" slot in plastic and another to cut 4 holes in aluminum, and both of them have >70% life remaining.
I'd jump on that. If you have a sharpening jig, you did spectacular.
I don't have a sharpening jig but I plan to make something.
 
I think you’re in good but not spectacular deal territory. A couple years ago I bought what looked like a couple hundred end mills from a closing machine shop, when I got the Takisawa TSL-800 lathe. Most were in good shape and I paid about $250, split it with a friend, so we both ended up with a bunch, about 70 to 80 pieces of larger diameter mills, in the 3/4” to 1.5”, all with 3/4” shanks. Many will had the wax from resharpening. It looks like this is pretty much a lifetime supply, though I hope not. :)
 
I like the little tool box...more pictures of the box please.

I estimate that it, like the end mills, has managed a longer life than I have, so maybe more credit is due, but in my opinion it's pretty unremarkable and you could buy a better one at HF. I can't find a brand name anywhere on it and it's made of thinner sheet than I would have the gumption to make a toolbox out of. I assume it's either old asian import or the cheapest American made that money could buy prior to the proliferation of Asian imports. But beauty is in the eye of the beholder, and you asked, so here are some pics:

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Here are better pictures of the weird stepped mills:


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The largest diameter is .625"
The medium diameter is .590"
The small diameter is .485"
The stepped sides are straight, no taper.
 
I haven't bought used end mills because I don't have a means to sharpen them, but that looks like a decent price for what you got. You can easily spend $100 on just a few quality end mills. I've bought used lathe tool blanks though. I paid around $30 for a small USPS flat rate box full, so I'm set for HSS tool blanks for quite some time. The blanks can also be interesting when you get some that were sharpened for special uses.

I've had no issues with my Chinese end mills, but I've mostly used them on aluminum and brass. The machine pushing them probably makes a difference too, a 2 or 3hp mill will be more demanding of an end mill than a fractional hp mill.
 
I've had no issues with my Chinese end mills, but I've mostly used them on aluminum and brass. The machine pushing them probably makes a difference too, a 2 or 3hp mill will be more demanding of an end mill than a fractional hp mill.
I was only joking about my experience with the Chinese endmills. I do have some and I have used them to cut plastic and aluminum but they're still like new. I haven't used them for anything precision so I don't know if they're absolutely straight or within spec or anything, and I haven't tried using them on steel (and don't plan to)
 
I estimate that it, like the end mills, has managed a longer life than I have, so maybe more credit is due, but in my opinion it's pretty unremarkable and you could buy a better one at HF. I can't find a brand name anywhere on it and it's made of thinner sheet than I would have the gumption to make a toolbox out of. I assume it's either old asian import or the cheapest American made that money could buy prior to the proliferation of Asian imports. But beauty is in the eye of the beholder, and you asked, so here are some pics:

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I'd lay money on that box being a Kennedy.
 
 
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