From the things you have written, I would say don't get it signed. I think the allure to you would have been the opportunity to have gotten it signed in person and it doesn't sound like that is going to happen. You mentioned the "romance" in asking for it to be signed and in the personal touch. Look at it this way, there is no romance in this potential business transaction, much like a hooker. He would sign it for $150 even if a serial killer was sending it to him. He's doing nothing special for you other then taking your hard earned money. I don't mean this to be demeaning to Stan at all, just trying to categorize it as a non personal business transaction. Since the dollar amount is material to you, I don't think you'd be happy if it looked like a chicken scratch. For the same $150, you could get a nice, flawless sig from his better signing days. It wouldn't have that personal touch to you, but remember, it wouldn't be a personal touch for him even if you send your own item in, it's just business to him and his family.
However, if I'm inferring wrong and it would mean a LOT to you to have his signature (whether good or bad) on YOUR particular item, then by all means, send it in. But, I think if that was the case, you wouldn't be asking the question in the first place.
Good luck and I hope you make whatever decision makes you happiest in the long run
Mike
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