1) "We searched 20,000 systems to find only the memory upgrades guaranteed to work in your IBM ThinkPad 390E." and only PC66 dimms showed up. So, I guess its safe to say that you cant use pc100 dimms. (Crucial memory finder)
2)Yes, I believe so, but the BIOS will most likely (99% sure) say that the hard drive is too big and not recognize it. There may or may not be a way around this.