I never finished Skyrim, got kind of bored with it around level 20 or so... Didn't get too far into it. Do you think this DLC would be enough to get me into playing the game again, or a waste of $20 for me?

Waste of 20$ for you

Maybe it's worht waiting until all the DLCs are out.

I had the same problem with new Vegas. Just couldn't get into it. I eventually got the ultimate edition, got through most of the game. Unfortuantly, i ran into a major-ish bug and ended up quitting, but it did get me out of that hump.

You have to finish the main quest pretty much to play the DLC,

SPOILER!!!!!!!




because you'll need the elder scroll from the end.

This.

No you don't. When you need to find the two Elder Scroll's it takes you to where in the main quest you go and get the Elder Scroll. No need to do the main quest to start the DLC, just need to be level 10 or higher to start it.

Either way if he didn't get into it then he won't want to go to Alftand through the biggest ruine in the game.