Lots of good advice in this thread. I am relatively new to Lugers and started by seeking a matching WWII era shooter as well. My experience:
-Knowledge and patience are key. If you are short on either you are at risk to overpay, buy a poorer specimen or both.
-Knowledge sources: books, visit shows, talk to collectors, read the forum(s).
-Matching WWII (Mauser) shooters are a bit of a tricky proposition. These are desirable and therefore tend to cost a bit more than other eras. A matching WWII (Mauser) Luger with good or better everything (bore, finish, grips, function) costs $1,100-$1,500 between collectors, higher if purchased from a dealer. As finish, bore, grip quality declines or parts begin to mis-match, price declines. But there is a range. It takes some combination of work, patience and luck to find good weapons toward the lower end of the range.
-I would counsel get a relatively inexpensive shooter, enjoy it for a few months and go from there. My first Luger was an all-matching WWII Mauser with significant finish loss but an excellent bore. I learned that it makes me very nervous and detracts a bit from enjoying the shooting experience to fire an all-matching gun due to the risk of breakage. I still have the gun and shoot it a little, but have since acquired a mis-matched WWII Mauser in good to very good cosmetic condition that I find more satisfying to shoot. I don't worry about breaking parts and it addresses my personal preference to shoot a nice-looking pistol. My point is, start with an inexpensive shooter and you will learn a lot about both Lugers and what you really want.
Good luck to you in your search.
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