If the guitar needs a set-up that would be money well spent. I would recommend Martin Retro Light strings - less tension, but still sound good.
I did the classical to steel transition a few years ago. You have to face the reality that it's going to take your fingers a while to get up to the task. I wouldn't play until they bleed (or are extremely painful) as you'll find they are still unhappy the next day. You'll get there sooner than you think, just play as much as you reasonably can each day.
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Keith
Martin 000-42 Marquis
Taylor Classical
Alvarez 12 String
Gibson ES345s
Fender P-Bass
Gibson tenor banjo
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