If DA, a good one is going to cost a bit. A new S&W 617 is about $650 and a good used S&W M-17 or M-18 or M-63 will be $500+ at today's prices. You can always opt for a Taurus or Charter - but they are not even on the same page quality wise - half the cost though.
I have an older Monson-made Dan Wesson and it's the equal of any S&W - they're usually available on Gunbroker for about $400...
Well, first of all do they want to go with a western style single action or the flip out hand ejector double action type?
For western style many will recomend the Ruger Single Six. It's an option that will not wear out and will deliver excellent performance for many years to come. It's also one of the more expensive options. On a cheaper front there's some of the older Harrington&Richardson wheel guns or the High Standard Double Nine. Many of these are both single and double action and often have a way of bulk unloading and loading via a flip out cylinder (my own HS Double Nine does it that way) or via top break as found on some H&R models. There's also a lower priced single action option in the Heritage western style. Inexpensive and there's reports of some heavy trigger efforts but on the whole the reports I've seen were all positive.
Next are the S&W options be they new or used. These would be hand ejector types that are single and double action. They are all pricey. More so than the Ruger even. But like the Ruger they will work for years to come and can be used by any member of the family to put a grin on their face. Lots will say that a model 17 or model 22 are THE .22 wheel gun. Some other options that will fit smaller hands are the Model 63 and the old Model 34. Both use the samll J frame and are lighter with a more compact grip. The nice thing about these lightweights is that there's a little more kick than from the other heavy options. I like it because it gives enough feel that you know you're shooting something but the recoil isn't enough to startle even the most timid new shooter.
Taurus 94's have a very faithful following as well and while still pricey can be had for much less than the S&W options for the most part.
For SA a Ruger New Model Super Single Six. It comes with 2 cylinders, one for 22LR and the other for 22Mag. Depending where you live it'll run around $450 - 500.
A Single Six runs right at $400 NIB for a blue model. You don't say what age the boy is, but a young'un might be better off with a Bearcat. Every bit a Ruger, but on a slightly smaller scale.
Taurus 94s can be had for less than $250. Love my 5" with wood grips, 9 shot cylinder, target sights. Not finicky about ammo. Smallish grips (for me) great for youngsters.
For affordable .22s, I recommend checking out H&Rs. They're cheap, rugged, reliable shooters. Just as I wouldn't give a new driver a 'Vette for their first car, I wouldn't buy a $500 .22 for a first gun. If they like shooting and are careful, then, if they want something a little more polished, I'd consider the S&W.
This H&R double action convertible six shooter cost me around $200 last year. It is one heck of a tack driver. I have a 1961 Single Six Magnum Model and this H&R shoots just as good, if not better, in SA mode. In DA, the Ruger can't compete at all.
The H&R non-convertibles hold 9 rounds and also cost less. They're all over Gunbroker for cheap. This DA 929 with the swing out cylinder cost me all of $92 a year or two ago:
This 929 is a remarkably accurate shooter with a fantastic DA trigger and it cost all of $59.00!!!
Let me piggy back on Woad_Yurts H&R reccomendation! For ~75 years H&R (and later NEF) made working pistols. They are not elegantly finished, nor do they have triggers like a Colt OMM's. They are inexpensive and reliable revolvers that get the job done. If you are diligent you can still find .22's (and .32's) in LNIB shape for less than $100.
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