Estate planning question

I recommend maintaining a file with all your purchase invoices so your beneficiaries will be horrified by how much you spent on your gear

Also, I have a couple relatives and because I’m a really mean spirited person I plan to give one of my main speakers to one and the other main speaker to the other and let them figure it out.

I keep a personal file with all my passwords and other info on how I process on my bills between credit cards and direct bank payments so people can follow my monthly financial activity which is a very nice thing to do. This info also includes a list of beneficiaries for all my accounts which is also nice to do.

Try not to include percentages as to how your estate will be split up because that just means it will all be appraised and liquidated.  This will make it difficult for your family members to pursue what they want and that’s really sad. recommend individually identifying who gets what for the significant items, that’s a very humane to do and that way key family items will not be required to be appraised and possibly liquidated by estate sale which is absolutely horrifying and a great way to diminish the value of everything you have. Don’t put your family members in a position where they have to pay what the appraisal says it’s worth to purchase something you want from your estate.

specifically identify your equipment to individual beneficiaries as best you can and then if they choose to sell it they can do it at their leisure and maybe they will come to love it just like you did. That way you don’t have beneficiaries, executors and liquidators being at the mercy of appraisers, etc.

Try to anticipate the final accounting process of your estate and make it as simple as possible to avoid incredible stress by those trying to settle your estate and obviously to reduce attorney fees. 

You should have some options in a town as big as Chicago.  There's a Chicago Audio Society - sure to be several people with the same questions as you.  As mentioned already, there are also many audio stores in the area, several featuring used equipment.  Have you checked Saturday Audio Exchange or Chicago Audio?  

figure out what you want first:

• easy process
• good home
• highest price
• please the family

You can't have all 4. They are kind of conflicting goals.

I think expecting 25% is realistic because the dealer will drop the price to 50% of the value and will keep half of the proceeds. 1/6 is pure greed.

Being in the business for for well over 30 years I have seen this scenario several times. I would personally recommend contacting all the high end dealers within 50 miles or so from your house and have them come over to inspect all the gear. Let them make a cash offer or sell on consignment. Then have them pack and move the gear out with a complete list. The gear is then out of your space and you have the cash, or you get payments as the gear sells off. It's better to work with a local dealer, especially if you have purchased from that dealer. 

OP might want to investigate the Saturday Audio Exchange on Belmont in West Town.  People there might have a recommendation for him