Thanks for the tips everyone.
So it sounds like the airless are the way to go if I want a good unit. I am almost done painting my entire house walls inside, and I had vinyl siding installed late summer so I guess i'll have to see how much I want to invest. Next paint projects are interior doors, some louver style bi-fold doors, and then eventually cabinets. I'm hoping to take bob up on his invite to see the different types of painting systems he has. I might also pick up that Critter spray gun I mentioned above for $39 since I am always building or doing something that can use some paint, and it seems to be a good gun to shoot just about anything through with my 6 gallon pancake compressor.