Dr. Know -
I know exactly where you're coming from. Incidentally, I lived in Dallas and Arlington a looooong time. Where are you located?
I also "push pixels" for a living, and frankly the best place to start with an Amiga - in my opinion - would be an A1000 or A500 barebones stock just to get your feet wet. (For FSUAE, same thing. Keep things simple like you were in 1987 again.)
You could get by quite nicely with a small hard drive upgrade of some sort, then install Deluxe Paint III. That's where the magic really started to happen on Amiga in a big way. For the past few years I've created a couple images that I'm pretty proud of at a stunningly small 320x200 (stretched to fit a monitor) at 16 or 32 colors max. The Amiga can do much more, but that's a pretty great place to start just to learn the tools.
Once you get that under your belt after a few sessions, you'll be on your way! I made
a video a couple of years ago showing some of the basic tools.
Anyway, I hope some of these images I made inspire you to keep going, keep pushing, and show us what you come up with!
Note: if you make things on your computer, be sure to stretch the 320x200 to 4:3 after you're done in Photoshop using 'hard edges' or everything will look like a smushed postage stamp.
Sad to admit I didn't produce a piece this year for the
Amiga Art Contest, which is always fun to participate in.
Welcome to the site! Hope you have fun and I look forward to seeing what you come up with. If you run into any questions or troubles don't hesitate to ask. Someone here will bend over backwards to help, I'm sure.