I own most of the pistols being discussed here...
My FiL and I both got good 1911 copies for under $400. Mine is Turkish and his is Filipino. The sights on the GI models are small. His is a better shooter because it has bigger sights. They are both reliable, accurate, and fun.
I still have the FEG High Power clone that I bought barely used in 1988. It fits most hands well and points nicely. The sights are small. Surplus ones are $350ish or so. Mine still functions perfectly after all of these years.
The Tanfoglio CZ75 copies are some of my favorite handguns. The steel ones are classic. I got a surplus Israeli 9mm for around $330ish and it is exceptionally accurate. I got a target model 45acp with adjustable sights used for around $400. (The polymer ones are not as "classic", but they are cheap: I got gently used examples in 45acp and 40 caliber for $249 apiece in the past few months.)
The CZ82/CZ83 is a very nice pistol. I like my Russian Makarov, but the CZ's are a little more refined. The 82 is 9mm Makarov and the 83 is 380acp. My Fil and I both have 83's. They cost around $250 and $300 respectively, and are accurate and reliable.
There are various versions of the Tokarev pistols in the original caliber and in 9mm luger out there for not much money. I think I paid around $200 for my Chinese one in 9mm. It works just fine.
I have a Taurus clone of the Beretta 92 and my FiL has an older model military surplus version. They are both good solid guns with good sights and decent triggers. Surplus they are easily under $400... probably more like $350 or less.
My surplus Beretta 84 is another nice pistol. It was around $330 with a lot of holster wear, but not shot much. It is a nice pistol similar to the CZ83 (which I slightly prefer).
My Star Super B in 9mm luger is one of my favorite pistols. They were selling surplus ones for around $200 a few years ago. My FiL ordered one as soon as he shot mine. They are quality steel pistols that handle a lot like a 1911.
IMHO, places like CDI Sales (Gunbroker), AIM, Palmetto State Armory, etc. are the OP's friend. Milsurp and police turn-ins are easily the best value for the money that is out there. Mine have mostly been carried some and shot little. If the OP wanted good shooters with a worn finish, he could possibly find two of the above pistols for $500 total. Getting a nice-looking and reliable classic pistol for around $350 is very easy if you go the milsurp route. I would recommend the Tanfoglio CZ75 copies and the CZ83's above the rest, but there are lots of good ones.
This. 
