hmm... don't know how to approach this one.
There seems to be a big gap in the prices of paint guns, and I suppose it's mostly about how much you use it. I'm of the mind that it's really tough to get a decent gun for much under $300 (I take that back, I just looked up some cheaper Devilbiss guns). And it's hard to nail down exactly what makes them better so it's hard to justify to someone who doesn't paint but if you do, it's night and day. The pattern of spray and atomization of the paint is going to be the biggest differance, you'll find that with a low end gun you'll waste a lot more paint and struggle with the finish than with a good one because the droplets are physically larger (which ironicly gives you much less coverage) and going more or less everywhere. The level of precision machining that it takes to break down the paint and mix it properly in the head is not cheap and you'll pay for it. I have a $30 Kobalt that I picked up for home use and it's just barely a step above a rattlecan. The trigger actuation and control is going to vary widely also and you'll find that cheaper guns normally have fatter needles, these traits can make the gun leaky and/or unpredictable. It's much like the differance between a Harley and a Ducati.
My recomendation would be to get a small version of a good gun, like a Sata Minijet, or a Devilbiss. (you can get a hold of a Devilbiss for not much more than $100)
Go for a gravity fed, they're more gracefull to handle, the flow is more consistent and you won't be doing anything large enough to have to comprimise to a siphon.