Does length dilation affect the Y axis in the Nether?
According to this thread in the Minecraft Forums that seems to have peeked into the code, length dilation does not affect the y-axis.
http://www.minecraftforum.net/topic/345806-nether-portal-science/
Summary version
Calculate coordinate of destination based on entry coordinate. (X, Y, Z) <---> (X*8, Y, Z*8)
At destination, look for the closest active nether portal within a 128 block radius of the player (257x257x128 area centered on destination) (the Euclidean distance (the 3D distance)). Teleport player there if one exists.
If no portal exists in the 128 block radius, the game creates one by looking for the closest possible nearby position within a 16 radius column (33x33x128 area) that has enough space to spawn a portal. And teleports the player there.
And if there's no possible spawn position with solid ground, it just creates a portal at the destination anyway, converting any blocks in the way into a portal.
According to the wiki:
If you place two portals on top of one another you will come out of the bottom one on the overworld and the top one in The Nether.
I read somewhere (I'm afraid I can't remember where) that a portal will always(?) connect to the nearest portal in the other world. Thus, the Overworld portals should connect to the nearest/highest Nether portal and the Nether portals should connect to the nearest/lowest Overworld portals.
This theory agrees with the wiki and with your received behavior.