I don't think anybody will be able to say with conviction if X or Y car is a potential money pit over the next few years... it really comes down to buying a known good one and ultimately, luck. That's just the joys of used cars and on that note you could buy the cheapest, most neglected example and it'd could give flawless service or you could blow your budget and then some on the bet of the best and it could fail terminally and leave you with a huge bill.
As for when is best to buy... again that's really down to you're own circumstances and outlook on the matter. If you're unsure and feel you'll always be questioning your decision, don't do it and sit tight. But equally, life's a bit short so if you're in a position to buy and you see something you like, just take a chance - it might be great, it might not but all you can't do is mitigate the rik by doing your research, finding a good one and then hope it works out.
As an aside, have you considered and XC70...? £10k buys a very nice one.
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