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As far as the Settlers series is concerned you should try the official board . There are many people playing the games (or attempting to play the games) on XP/Vista and later.
I know for a fact that Settlers 2 can run on Windows Vista because gog.com re-released it with Vista compatibility. Usually Good Old Games (gog.com) only do the stuff that users don't want to do themselves, meaning: searching for solutions to make old games compatible with XP/Vista then releasing them with a new installer (and the authorization of the copyright owners, of course). However solutions exist for most old games without the need to go through services like GOG if you have the original CDs. The only thing is that it may take some research, downloading, tweaking and hitting the right places (like the link I mentioned above for The Settlers) before getting the game to run flawlessly on the latest OS.
To answer your first question, if you never got a game to work on Vista then there is little luck that it will work better on Windows 7 so spending more money for a newer OS is not the solution. However if you manage to get a game running on Vista, the chances that it will also work on Seven (using the same tips you applied for Vista) are pretty good.
The only advice I can give you is to start with a search in your favorite search engine (Google, Bing.. whatever) on the web for the title of the game you have in mind and 'Windows Vista' (For example for Settlers 2 you'd type in 'Settlers 2' 'Windows Vista' -- quotes are important since they tell the search engine to look for Settlers 2 and Windows Vista on the same page rather than looking for any of the word hence that will spare you a huge number of irrelevant results) then look at the results. Depending on the game (Is it well known? Does it have a good user community around it?) the chances to quickly find and answer to run your old games on your system may vary. You'll generally be able to find quicker reliable solutions for games that are followed by a strong community than for games that nobody even remember. Some old games with a huge fanbase have community websites already there to help you and that probably already have all the answers (like the Thief series with ttlg.com). On the other hand you may be out of luck if you have a game that few people care to play.
Good luck with your researches..

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