I happen to have a SP2022 and a P229 sitting n front of me right now. I have a P228 in the safe as well.
Both are fine weapons. Both do the Concealed Carry role pretty well. I tend to carry mid sized 9mm's, so both are right up my ally as far as what I like. So with that out of the way:
2022:
It's cheaper and lighter. It's also just a little bigger, both feeling in the hand, and in actual measurements. It has a VERY good DA/SA trigger out of the box, and is an easy gun to shoot well. I just relooked at mine, and while I can see the LCI at the bottom of the rear sight, I have to look for it, I've never noticed it while shooting. The 2022's LCI is much smaller and unobtrusive than that abortion Sig put on for the 226's for CA. I haven't had a problem getting holsters for the 2022 (I have a Leather IWB, and a Kydex OWB) but I did have to order them. You're unlikely to walk into a store and find them on the rack. Mag catch is reversible if you're sinister handed (I am). As was mentioned upthread, the pinky extension on the mag comes up into the front strap quite a bit so you can pinch yourself pretty badly doing vigorous reloads.
P229:
I have a 229 Legion and a 228, so given that you didn't ask about the super expensive one I'm going to kind of merge the two guns for this comparison.
The 229 balances better with a full mag, and is heaver so it seems to handle recoil better. This gives me measurably faster splits and target transitions. I have Houge G10's on my P's and they fill your hand "just right" Pretty much everyone that picks one up likes the feel. (My 2022 has crimson trace's for comparison) The P series has much more aftermarket support. Stock, I honestly think the 2022's trigger is just -><-
that much better, but if you get a model with, or add an, SRT kit to the 229 it takes the lead. Holsters are more common.
Honestly it's a hard choice, and it kind of depends on personal factors. I already owned a 2022 when I bought my Legion. I think the 229 legion is a better combat handgun than my 2022. I have targets and a shot timer to prove it. But it better be; it was almost 3 times more expensive. (I bought my 2022 used for $399) That said, I slide my 2022 into a holster and leave the house and don't feel under gunned at all. It's a fine combat handgun that I have, over thousands of rounds, learned to use quite well. What are the odds on any given day I'll need that extra 2/10's of a second?
Both handguns are so reliable as to make no practical difference. I haven't had a malf (yet) with the Legion, but it's obviously kinda new. The 2022 had a couple weak ammo malfs back in the day, but it's 3 or 4 over the course of probably 7000 rounds and 7 or 8 years. Statistically a non issue.
It also depends which model of 229 you're going for. If you're looking at a base, stock, Nitorn 229R vs. a 2022, I think it comes down on the side of the 2022 just for value's sake. If you look at them more feature rich 229's (Legion, M11-A1, SAS, Scorpion and whatnot) then I think they start to offer enough over the 2022 to make the price differential more reasonable. Some of it will depend on how much disposable income you have. Either way, I doubt you will be disappointed in either gun.
