My father bought a used Sawzall years ago, which was a major purchase for him at the time. It came from an estate but before passing away the previous owner had gone through everything and told his wife what each item was worth.
I have that plan in motion also.
Regardless of my purchase price I have made a list of "fair market used' prices.
Yellow or green B & D drills are at $2-3 ea while a Milwaukie Hole Hawg would be probably at $200.
My General 16" planer (not int'l but made in Canada will list in the $1000 range.
But then I consider myself a 'tool nut'.
In my collection I also have many pricy specialized aviation tools as that was a former talent.
Includes torque wrenches, specialized cylinder wrenches, tensiometers as well as a selection of rivnut tools.
In the pneumatic tool department I lack very little and that from aviation to construction tools.
Bet I have close to 20 pneumatic tools from drills to nail guns.
(I did switch careers some 15 years ago)
I'll also add that my SIL is also a practical (wise daughter) kind of guy so he'll (after first picks) help my better half to get best $$'s for my collection.