I am perfectly content with my 1st Generation iPad, as I barely use it to begin with unless I'm traveling.
The biggest factor that will ever get me to buy another iPad is if Apple finally intergrates a USB and HDMI slot.
I don't know if you have followed Apple a bit lately, but there is just no way that Apple will integrate USB. There is no reason for them to change away from the universal connector. In addition Apple will most likely focus on Lightpeak / Thunderbolt for data transfer, and will most likely supply or start selling a universal connector for that interface soon.
Apple has much more control over peripherals with the universal connector, and Apple earns a lot of money by selling licenses for universal connector peripherals.
About HDMI: same story..