what do you think of the first attempt? be honest

 

pretty good but the blue needs to be bigger

 

I'm not sure. My initial reaction is that it's too 'busy'. I think that the oval shape works against what you're trying to do. Perhaps a more 'abstract' flag would be better. Like no stars (since you're not going to get all 50 on there anyway) and fewer stripes. -or- a rectangular flag that does not fill the entire oval.

Just some ideas. I know I don't have the talent/patience to do it.

 

i agree with the less stripes. just imagine a view of about one quarter of the flag showing. that way you can maybe squeeze in some stars in the blue area and just show a few stripes.