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A lot of good points in here already.  I'll just add this one thing I've seen from people in similar situations where they advertise an entire shop worth of equipment being sold on this day, at this time. So, not selling everything as one lot, but basically a one day garage sale. That'll clear out the most desirable stuff and then what's left over... Maybe that gets donated or sold as a single lot.  I wish i was closer to you and could help take at least some of it off your hands. I'd be glad to take a look at any hand tools he's got - chisels, planes and saws and make you a fair offer on anything of interest.

Von makes a lot of good points.  Personally, I'm not on facebook so it would be Craigslist and Nextdoor for me.   Selling price;  Unless something was especially valuable, I would be between half of what I paid and half of the current new price.   I'd still check out estate sellers.  You can go to estatesales.net to see sales and sellers near you.  Another thought is an auction house? 

1/2 the price of new if it's in good condition works. But I would start at the price of a new equivalent as prices have increased quite a bit lately. For anything like Festool, Woodpeckers, or Starett, I would price it 20-25% off.

I think it's fair to say there is a trade-off of money versus time/effort. If you want to move stuff along quickly, sell it cheaper or give it away. If you want to make more money, it's going to take more time and effort. I suggest making sure all the stakeholders are in agreement. One way these shop clearings can become difficult is when the shop owner (or their representative) unrealistically expects things to go quickly and generate lots of income. You can also run into issues because of memory: "I paid $X for that! How can it only be worth $Y now?" Or if the owner is still around, emotional attachment: every time you start to sell something, there is a sudden change of mind. I don't mean to dissuade you in the least, but we've spent some time discussing these clear outs in the local woodworking club because they come up regularly and lessons have been learned, so go in with your eyes open. Also don't underestimate the effort just to go through stuff and price it - we tend to pack our shops tight, which is not an easy state from which to sell stuff. Think about how much space it would take to spread out a shop's contents for sale... The one case I was personally deeply involved in went smoothly as the widow had her priorities clear and consistent: she wanted her garage back and would compromise on price to get there. Even still it was six months of steady off-and-on work to clear everything out. I'm watching another one play out on CL that has dragged out for over a year with no apparent end in sight.

I get it. This is all funny to me. They complained that it was “hot” when we moved here in July, and it was 97°. How do they feel hot when it is 84° in Feb.? I think maybe it’s a humidity level they don’t like here. On a more personal note, I have my first Cattleya about to bloom. That’s a win for me.