You can't go wrong with any of those. They're all classics and cornerstones of a legitimate gun collection.
I'll tell you what I'd do, but if you're not the patient type, you can stop reading now.
I'd suggest saving some money, doing some research, and knowing what constitutes a "deal" on any of those guns, specifically with models you're interested in.
Go around and look for used specimens and let fate decide.
You'll likely be able to find a beautiful S&W Model 19 for $300 if you look long enough, or other comparable deals.
I see no reason to empty your pockets ASAP (read: the "B"-word), so you might as well stretch your money a bit, and have some fun learning a bit and ogling guns while you're at it.
P.S. The value of a .22LR pistol can't be overstated either; You might be able to have more fun for $300, but it won't last the rest of your life like the pistol.