Start selling pieces from my collection now, or wait a while?

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So the process begins. I have listed in our private watch sales forum the first one - a Constellation Calendar from 1958 that I think any aspiring vintage Omega collector should consider. If it does not sell here I will go to eBay. I will go on offering the others here in succession, as I want to give my fellow OF acquaintances first dibs.

I'm looking forward to your listings.
 
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Thanks, @Zman4eva. I intend to give each one a month on OF, so the next will come up in early February.
 
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Thanks again to all who responded to my post. @pdxleaf and @Spacefruit in particular made excellent points. I would have taken the road of an auction sale of the lot, but in Australia there is no auction house I know of that would give the watches the attention (eg good photographs) that they deserve.

So the process begins. I have listed in our private watch sales forum the first one - a Constellation Calendar from 1958 that I think any aspiring vintage Omega collector should consider. If it does not sell here I will go to eBay. I will go on offering the others here in succession, as I want to give my fellow OF acquaintances first dibs.

I am sorry you are having health issues. I think you are taking the right approach, a careful measured sell off. Having lost my father a few years ago, I have some experience. He left my stepmom a pile of stuff to deal with, but did designate a friend to help her with his gun collection. Regardless, it was a project for her. He left his Speedy to me which is what really sparked my interest in watches. He had not worn the watch since the 70s, and I am sure he would have been happy to see me enjoy it so much. I think it is something that we could have bonded over. So if there is anyone in your family who would appreciate your watches or other possessions, I would encourage you not wait until you are gone to pass things on.
 
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I am sorry you are having health issues. I think you are taking the right approach, a careful measured sell off. Having lost my father a few years ago, I have some experience. He left my stepmom a pile of stuff to deal with, but did designate a friend to help her with his gun collection. Regardless, it was a project for her. He left his Speedy to me which is what really sparked my interest in watches. He had not worn the watch since the 70s, and I am sure he would have been happy to see me enjoy it so much. I think it is something that we could have bonded over. So if there is anyone in your family who would appreciate your watches or other possessions, I would encourage you not wait until you are gone to pass things on.

You are right - one son is definitely interested in one of my Speedmasters, so that won't be on offer. However as there are about 25 watches I doubt he would want them all, but on your prompting I will check with him.
 
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Sorry to hear of your health issue. I’d start thinning out the herd. Recession or not, the pool of serious buyers is shallower compared to a few years passed. I’d spend a week listing them on all platforms and let them go. Your remaining time is most valuable to you and family.
Edited:
 
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You are right - one son is definitely interested in one of my Speedmasters, so that won't be on offer. However as there are about 25 watches I doubt he would want them all, but on your prompting I will check with him.

I don't think you will regret the decision. My Dad and I had the talk about what things I would want to inherit, which was good. However, now that they are in my house and I see them everyday there are questions I would like to ask him about them, but it is too late.