I wouldn't worry about Err99.
I would however sit down & think what is it you're looking for in the new camera. 40D may or may not be the answer.
When I had XTi (400D) I thought upgrading to 40D would let me take better photos. It didn't. For all intents and purposes XTi was every bit as good IQ wise, and I didn't really care for the added weight and bulk. Sure 40D had a lot of improvements but they were all in the areas I didn't really need. Luckily I bought 40D in Costco so I had no problems bringing it back.
I finally upgraded to T2i, a couple years later. It was primarily done for the video. T2i also has some visible improvements in the IQ over XTi when using high ISO. However I can honestly say that I would have been just as happy staying with XTi.
Now I don't know how 300D compares to 400D. Assuming the IQ is close, and if the money is tight, perhaps you would be better served spending it on something else - lenses, flashes, etc.

