I'd consider a Yam TTR250...it's probably the last affordable proper Japanese trail bike without the encumbrances of water cooling and all that.
DR350Ss, XR250s and 400s are all fetching big money now, as people realise the virtues of the old-school bikes. The Yamaha 250 will surely follow, so it's the kind of bike you can buy, try, and sell on without loss if you either decide that trail riding isn't for you, or you want something more modern as the 'next step'.
Alternatively AJPs, which use old-school engines in modern European chassis, are good if you can find one that hasn't been 'teenagered to death'.
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