I'm one that's on the side of HVLP gravity feed guns. Siphon cup guns will dribble paint when held at odd angle also, through the vent on top of the cup. Trick is with ANY gun, keep 'em back away from your target when holding gun at weird angles... It's all what you get used to...
I have a couple "Huskee" guns (Home Depot) that were around $60. Also have a Sharpe platinum gun that was around $300 IIRC. The more expensive guns seem to handle "high tech" paints and finish's with a little more consistency, but as Chris eluded, it's MORE about technique....Practice...Practice...Practice....
I compare paint guns to golf clubs...Not every club fits the style of every golfer. Same applies with paint guns. Find yourself an automotive paint vendor if you can, and let them walk you through the various types of guns. You're under no obligation to buy one, just let 'em know you're "shopping" but maybe not BUYING....Most will be glad to show you the ropes.
A reg is essential. I DO NOT like 'em hanging on the gun. Extra weight can be cumbersome after prolonged use. I have a reg on my compressor, and will sometimes put one in line, a hose length away from the gun when I feel the need to "micro manage" air pressures. (when painting large surfaces AND small parts at the same time)
Get a GOOD water trap.
Make certain your compressor has enough cfm's to keep up with the gun. There's another BIG plus with HVLP guns....Lower air usage. HVLP guns will also cut down considerably on paint usage with a LOT less over spray. MOST of your paint will land "on target" as opposed to settling on the floor.
Get a GOOD mask, use proper ventilation. I have some symptoms of asthma which ISN't asthma....It's the effects of icocyanites (sp?) the catalyst in paint hardeners. It took ONE SINGLE EXPOSURE, less than 10 minutes......Some people are FAR MORE prone to the effects. Once you find out you're one of the lucky ones, it's already too late.
Get yourself an old car hood, or some similar piece of sheet metal. Practice on that. Try your paint/thinner/hardener mix.....Try your technique....Better to mess up that than the hood on your prized antique tractor......BTDT, sanded off a few horrible runs.....
Prep is EVERYTHING as Chris stated. Paint is NEVER any better than the surface it's applied to. CLEAN everything.
Tip of the day....NEVER allow ArmorAll NEAR your paint shop....Trust me on that one. Leads to heartbreaking results, let me tell ya...