A Hipower would be a good buy, as they announced they're going to stop making them. Other options would be a CZ75, of course a 1911 (you don't get anymore classic than that), Makarov, P-07, PPK, Desert Eagle, Gen 1 G17, early Ruger Mk series, etc.
Smith and Wesson Highway Patrolman model 28. It's the "Economy" version of a pinned and recessed model 27 and still can found for fairly reasonable prices if you have the patience to look for one.
Gunbroker is the place to look and your best bet is a reputable dealer rather than private party. Search every page on gunbroker from the first to the last. Some guns will start oout at a los price but bidding may ore may not drive the price up. As I said, it takes patience.
A K-frame model 19 or 66 may be easier to find but the N-frames are more durable and "round count" is less of a concern.
Absolutely, more money (if nothing in price range). Since the OP has a lot of guns, there is no hurry. So save up for whatever he really wants to get, price not a factor
Depending on how you define classic I'd look at the following
Colt Single action Army
P 08 Luger
Walther P38 first DA/SA auto
Browning P35 High Power
S&W 39 first American DA/SA auto
Colt 1911
S&W 29
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