I always thought the 'message' of Second Chances was a bit skewed. Ultimately Tom Riker is a younger Will Riker brought forward in time. He's the ambitious young career man who flirts with Deanna Troi but takes the first opportunity to start climbing that career ladder again. The episode starts out by trying to make us buy that maybe this 'younger' Riker has learnt lessons that Commander Riker never did, that his isolation on the planet and his career having stalled (as opposed to Will's apparently meteoric rise from baby-faced Ensign on the Pegasus through to first officer of the flagship in the space of only about six years
according to the Okuda chronolgy) has taught Tom to appreciate what he didn't
get a chance to do. But then it drops the bomb that, hey, under the surface he's still Will Riker, and he's more than happy to dick around with Deanna's feelings again
(although at least he's got the balls to actually rock up and say goodbye to her this time around). The ultimate message seems to be, hey, Riker is still Riker no matter what. Which makes the episode a little pointless IMO.
Yes, Tom adopts a new name and ultimately takes a very different turn of character when he signs up with the Maquis in DS9. But in terms of Second Chances alone, there is just something a little off about the way it feeds us one message, about 'the road not taken'... and then does the complete antithesis of that message in practice.