I am a reseller. Sorry I didn't get to you earlier. Here are some things to consider:
Your time is worth something.
Even a kind gesture can turn into an overwhelming task.
Sometimes you have to have the courage to say no.
I have come into situations where the owner/spouse has had unrealistic expectations for the value of the things they have and they insist on selling them as a lot and getting their price. I have had to say thank you for the opportunity but these items are just not for me. In truth, even breaking up a large lot like that, overpriced items won't sell except to the most ardent collector. Selling to the best collectors takes knowledge, experience and connections with those collectors (and/or eBay)
Most times they find out that private buyers might not want ALL of those items or that they just can't afford to spend the money on tools that they don't want that they then have to sell.
As a seller, one has to decide how much their time is worth, how long it could take to sell the entire lot and how much more than minimum wage they want to earn for their efforts. Add the cost of storage and transportation if the items have to be moved off site. In the end, some tools won't find a new home and you have to decide what to do with them... I take them to local auctions, get what I can and let them be someone else's headache.
GOOGLE SEARCH IMAGES using words to describe your items gives you a shortcut to finding out what others know about an unusual or rare item. Clicking on the image usually shows you a page with more information about the item which you can then use to refine your search. Once you have key words you can go to eBay.
EBAY is an excellent resource, even if you don't sell anything there. By looking up completed and sold auctions you can find out what the market says people are ASKING for an item and what an item is actually selling for (to me, the transaction price is what a thing is "worth"). Key words are important.
SELLING on eBay IS TIME CONSUMING. I try to limit sales to items worth $50 or more so that I can at least end up paying something for the item and making minimum wage in the process. It takes me about an hour to take the pictures, edit them, write the description, answer any questions that might come in, pack, insure, ship and track those items. It can easily become a full time job.
If you're going to try to sell on eBay, these are my two most basic rules:
Take pictures that show every aspect of the item. What makes it valuable AND what might be damage. Take pictures as if there is no written description.
Write the description as if there are no photos.
Doing these two things shows that you have "done your job" and know about the item... There are a long list of other odd things you pick up over time that help improve your ability as a seller, but that's a book not this note.
You didn't say what you know about these tools or how much help Rue can be in getting things ready for selling. If he's a club member (I often attend 4 or 5 a month myself) those people almost always want more tools, see if you can bring tools to sell at those meetings. If your prices are right, they'll sell.
GARAGE/"ESTATE" SALE (you don't have to have passed to have an estate sale) can also be a great avenue for selling a lot in a comparatively short period of time... But you still have to do all of the research, pricing, setup, selling, take down, packing and storing what's left - and the tables and any other display items.
I hope this helps some
As a final note, kind of a self defense as a "liquidator," and not speaking for anyone else who does this, is I try and take all the things I listed above into consideration when determining IF I can buy a lot and what I can reasonably sell it for so what I can reasonably pay for the lot. I'm never looking to make a killing or loose my backside... Sometimes I do better than expected, sometimes I take a hit but these three things are true:
1) A person should get paid for their time and expertise
2) The marketplace, not sentiment or personal desire dictates the actual value of an item
3) Not everything has a secondary market value - or is worth enough to spend your time trying to sell... Sometimes donating is a good way to re person some items.