[continuing the thought that value includes where something is located]
You say that the original owner was in the Milwaukee area, but don't mention where the tools are now. I'm about an hour's from Milwaukee myself, and MIGHT be interested. However, I'd like to state right up front that I am a cheapskate (comes from years of necessity . . .), so if you can find a buyer willing to pay more, go for it! I am definitely NOT an expert on pricing, except for figuring out what I'd pay for some items for my own use. Something like the planer, I'd need to see the size and general condition of the machine, maybe figure out whether the motor is likely to be repairable, or replaceable, whether the rest of the mechanism is in working order, if it's on a stand or base of some sort, and on and on. And even here, location matters to some degree: if I need to find a trailer and tow vehicle, it would likely take a better deal to make me drive further.
Do you have a photo of each?