+1 on the comments that cleaning and ammo is the cause of most .22 jams. Some pistols just don't like some brands of ammo. It is not that all models of a pistol don't like certain ammo, it seems to vary by pistol. In general, I get my best results from standard velocity ammo. Cleaning, especially the slide, bolt face and barrel crown in the chamber go a long way into enhancing the reliability of a .22.
In the $250 price range:
S&W 22A: excellent accuracy and reliability. Reasonably good trigger. Easy to field strip and reassemble. This one seems to be built for SV ammo, but you can fire HV hollow points without too much consistency degradation. I almost never shoot HV ammo in mine.
Ruger MKIII and MKIII 22/45: The blued models are around $250. Accurate and reliable out of the box. Rugers have the advantage of a huge aftermarket for tweaks. Rugers are steady, reliable and solid pistols. First time field strip and assembly can be tough if you
don't read the instructions closely.
Browning Buck Mark: Excellent for accuracy and reliability. It rivals the Rugers and 22A in feel and shooting ease. I haven't had one long enough to thoroughly evaluate it, but I like the pistol so far.
Walther P22: Strong support and strong dislike for this pistol. Fun to shoot. Not nearly as accurate as the others I've mentioned. IMO (and that of a CS rep) the P22's are constructed of materials that are inferior to Ruger, Buck Mark and 22A. I've had one for 4 months, it spent 3 weeks at S&W and is now a "project gun" because I'm trying to fix manufacturing and design flaws in the pistol such as excessive slide wear and casings being ejected in my face (a result of a different slide coming back from S&W). Some folks never have any problems and some of us have problems. The P22 seems to shoot ammo that my other rimfires don't like. I haven't been able to achieve the accuracy with the P22 that I have with the others.
I bought the 22A for $175 (the 7" barrel in the photo is an add-on) and the MKIII 22/45 for $200. Both are great shooting, reliable pistols. Your choice should be based on how the pistol feels to you and what you want to do with it.