A Q6600 will outperform a 9950 most of the time and its $100 less (checked the egg this morning). So if you cant grab Q9950 you have some other options.
1. They have a set list of mobos to choose from, they aren't always the best bang for buck, or the best period in some cases. If you want to OC then you will need a decent board but most p35s, p45s. x38s x48s are decent OCers so its hard to go wrong, mostly it comes down to what newegg has on sale today.
2. Video ram helps you in higher resolutions. 1024x768 is really low, so I would say save you money and get the 512mb card. A good card to go with right now it ATI's HD4850. I have the 512mb model and it is awesome.
3. Yes, even though they only have DVI plugs the manufacturers are nice enough to include a little adapter plug. I have a analog monitor that uses vga and everything works fine. Although I highly recommend getting a modern digital LCD. The difference between an ancient CRT and a quality flat panel is too great to describe in words. Samsung makes great screens.