George mentions dust collectors. Probably the biggest dust collectors are the crappy $99 60mm refractors and the $199 4.5" reflectors, usually on almost impossible to understand (at least for beginners) EQ mounts. I agree that for $400 your best bet is a 6" or 8" manual Dob. $800 can get you a nice 6" SCT and $1200 can get you an 8" SCT.
I agree that no matter what route you take, a planetarium app for your phone or i Pad is a must have companion when you are out under the stars.
How about a good star atlas and a telrad? If you truly want to learn the sky, this is the way to go IMO.
As for scopes, I always tell people to start with a pair of 15X70 binoculars and a planisphere. Get a lounge chair, lay back and explore. You will start to learn the sky this way and not be out a ton of money if you or your kid looses interest. There is always time to buy bigger and better things as you become more experienced.
You mentioned the cheap refractors and reflectors which brings to mind something that really ground my gears one night. QVC had astronomy hour and they were pushing Galileo brand telescopes. 3" refractor and 4.5" reflector, about the same quality as the old Tascos. Then they were showng pictures taken by HST and telling people this is what they can see.
Talk about false advertising and a lot of disappointed people at Christmas.
George mentioned location and yes this is a big influence. Bigger aperture outside of town is good, but here in the city that light bucket is gonna soak up a lot of light pollution versus a 4" refractor. I think, like was mentioned before, an 8" Dob is the best bang for the buck in town and out for a first scope. 2 eyepieces (25mm and 8mm) and a 2x barlow would be a good beginning point. And like I said before, a star atlas and a telrad because while you are star hopping to your target you'll probably accidentally find 3 or 4 cool other things along the way.
Wolf.