I agree by technical standpoints, but small businesses have tough time to figure out what new features should be added. Software is an accessory for them, even if they cannot go without it. Most likely, many family businesses would not mind to 'stagnate' as long as possible. The only way to "wake them up" is to deliver new OS that will disallow to run old applications.
There is one more thing here: in business sense (regarding small/midsize business again) computer technology was quite able to provide full service long time before VFP6.

>One reason is that you get a better product to add new features to your app. All apps are being maintained. Better to add new features in the best, most efficient version of the app. I had one customer that used to ask me when the app would be finished (it was already live). I told them "when the app is finished, your business will be, too." An app only stagnates when a business stagnates and when a business stagnates it is starting to die. So maintainance can be done with the latest version so you have the best tools to work with. Another thing is that upgrading is really only a matter of recompiling. There is very little, if anything, that has to be done to a VFP 6 app to get it to compile in VFP 9 (unless you used ActiveDocuments). Another reason is simply to support VFP. If you think it's a great product, plop down $300 to support it.
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>>If you have some application running smoothly for years, why a company (esp. small one) should decide to upgrade, if they basically get the same product but still have to pay few days of consultant work?