Jairus, I'm with you:
Large cheaper compressor, and quick disconnect fittings.
I have a 5hp 20 Gal Coleman Compressor that I have in my garage and can use it for airing up the tires, using my air tools and just general stuff around the house. And I didn't even go the pipe and fitting route, I just ran a 30' hose along some water pipes in the ceiling to the model room!
Quick disconnect fittings connect everything. The long hose to the compresser, so I can take the compressor out into the yard if I need. The long hose runs right to the moisture trap (QD of course) which is directly connected to the regulator, with a QD on the other end. That way I can take them both out and use them elsewhere, like when I did some airbrush work on my 1:1 car.
As far as airbrush(es), I have an Aztek A4709 Dual action which I use for the 'good' stuff, and a couple of cheaper generic single actions for some of the other stuff like chassis and under carriage work.
I guess it's all what you're comfortable with and can afford, and I'll go the cheaper way if it lets me afford more kits!
JT