I can tell you, that many collectors who have acquired pieces out of passion and started some time ago have done very well with their watch portfolios.
Nevertheless, a positive cashflow on my balance sheet is necessary for me to continue to operate my lifestyle and for me to feed myself. This is true for all people, rich or poor, big or small. If you aren't profitable, you don't stay alive or in business.
I do expect wristwatch prices to drop from their frenzied highs to historical norms. I expect a return to normalcy in the market of wristwatches. However, worldwide wealth is growing; the Chinese are becoming incredibly affluent, and unfortunately the Chinese have quite an appetite for horological complications. Thus, despite the economic downturn in the West, I expect the East to pick up some of the wristwatches available for sale.
We live in an interesting time; but there should always be a fundamental rule regarding any collecting or hobby; think of the money invested as money that cannot be easily realized as money again. Don't expect good resale value, don't expect strong appreciation, don't buy art hoping that it will increase in value. Collecting should be based on pure desire. And when you do that, you will never lose. And if you do happen to see an increase in value on the pieces that you own; consider that as good fortune smiling upon you.