Several of the options you listed tempted me to vote for them, but ultimately I voted for you to buy WOZ. I own WOZ myself so can speak from first-hand knowledge. I doubt that it'll disappoint you and your family and friends. And if it does, I wager that you'd be able to sell it without too much delay or loss.
The idea of buying two pins sounds good in theory. But that said, and even though $9,500 is a generous budget, IMHO the $9,500 isn't enough to get two really good pins all in. For example, the two you listed, TOM and TSPP, aren't both obtainable in decent shape for $9,500.
I considered voting for one of the "wait" options, but I think you could get WOZ with confidence now, enjoy it, and then if a newly announced game seems super-attractive to you, sell one of your machines when the time comes to get the new one. (Bear in mind that any new machine announced between now and end of year won't be available immediately.)
All of the options you listed are good in some ways. I don't think you'll go wrong. Good luck!
Avondale, AZ
Orillia, ON
