There are two questions in the original post: will vintage speedmasters continue to appreciate, and will their value go down. Seems most likely to me that they'll stay about the same.
I'm not such a big fan of vintage watches purely as an investment. They might go up, they might not. But if you wear them, there's also risk: bang it hard, get mugged. There's also cost to keeping them serviced, and it would take some time to sell them if you needed to. And if you don't wear them, where's the fun in that? If you don't care about the watches as anything but an investment, instead see your financial adviser about some mutual funds. However, if you really like vintage watches and would regard possible appreciation as a bonus, then go for it!
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