It depens on what you call 'easy'. If you have made tons of customizations to the Free version then you'll need to do them again in Pro. If you haven't then it's just a matter of deleting the free version and installing the pro version.
On Dark Matter Pro you get indeed free 1.x upgrades. If there will ever be a 2.0 version it will probably be because Pixelpost 2.0 is here which I think will be a while. If I have to do a 2.0 version (I'll ONLY do this if I need to do MASSIVE amounts of work, in all other cases it will be an 1.x update. I'm not in it to rip anyone off!) there will be a substantial discount for existing Dark Matter Pro users.
Check out Dark Matter
, the accessible, degradable and sweet looking Pixelpost template.
Dark Matter Pro is now available at darkmatter-template.com
If you want something from me please DON'T PM me on this forum as the inbox keeps filling up. Send me email instead at marco at i-marco.nl. Thanks!