Well my mate has 94 gt legacy and it still feels like it definitely has near enough the 280 hp it came with from the factory. His has 280000 odd indicated kkms but being a Jap import it's bound to be more. He hasn't had any issues with his.
Can't help with servicing as he does it all himself.
The transmission would probably be helped a lot by an oil cooler and a Trans oil cooler if towing a lot.
The 2.5 is an older design but if a head gasket goes then replace it with a good quality multi layer steel gasket and you won't need to do it again. If it's naturally aspirated it'll be an open deck but that won't affect anything.
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