2 instance of iTunes?  Good idea, or bad?

I used two iTunes instances to sync calendar at work and music/applications at home. After doing this for the first time yesterday, my iPhone 3Gs did not function properly. Applications didn’t load (the would just pop up a splash scren and then go back to the menu) and I noticed the power indicator never moved from 100% all day. I did a recovery and it all works again.
I've had to re-download all the free applications, but the ones I paid for are asking me to pay for them again. How do I get those without paying again?
Also, what might have caused the issue in the first place? Should I not use multiple instances of iTunes? Both are newly downloaded in the last week, so they ‘should’ be the latest versions.

You definitely shouldn't have to re-pay for apps you already paid for. Are you sure you're logged in with the same account you bought the apps under?
If so: On the iPhone and iTunes it will look like you need to re-buy an app, but once you start the download it will just tell you that you've already bought it and it will download it again for free. Try this on one of your cheapest apps and see if it works.

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