"it's still a pretty brutal march at times to get to the newer, better content"

If the potential player you are talking to is only looking to race to the level cap, raid, etc, then you may be right that LotRO is not the place they should start. If, however, the player wants to take the time to enjoy the journey, I think LotRO can be just as much fun at level 5 (although these days you are at level 5 for approximately 2.7 seconds ;) ) as it is at 65.

Plus, the Turbine developers have even gone back to older content to revise here and there where they felt it was needed. So I never get the impression from them that they let parts of the game gather dust just because there is something new at the top.