The downside of thinking up 'projects' for yourself is there's no real-world pressure to get it done, and you don't encounter real-world problems that you would in a business application. Also, while it may be a nice idea to get a 'real' job and do this in spare time, with a family that's a lot easier said than done. To learn a new computer skill requires many hours of deep concentration, for hours at a time, not something you can dip into between making dinner and putting the kids to bed (for either spouse, I mean, not being sexist!).
It's true that in 11 years a lot has changed, and Android experience, for example, would be a definite plus on a cv. If a personal Android project was undertaken with a view to actually SELLING it/them on the Android Market and making some money from it, it might focus the mind better and provide better experience. Good ideas for apps, with global appeal, are obviously required first though. Other 'real world' projects, such as the stock app for the relative, would also provide realistic experience, but should be attempted in the latest technologies, e.g. Visual Studio 2010 / C#, perhaps 'cloud computing' (great buzzword for a cv, and easy to do with free/cheap cloud space from Amazon etc)