re: Chisel sharpening-Where to get started.

I'm still deciding-getting close. I've looked at videos in reference to the drill press sharpening setup and it looks favorable. The sharpening jig you could make if but its actually not expensive to purchase and the actual sanding system is affordable too. The only thing is you would need a way to sharpen the backs of your chisels before using that system and they have a prep kit for that as well.
 
As far as diamond stones go I've watched a few videos and they say all you need is a few diamond stone grits-a coarse and fine and then a strop and then you'll be plenty sharp.