After shelling out $80 for the base game, I'm in no hurry to pick up expansions, but if I like Descent enough I might get one eventually. What expansion do you feel is the most enjoyable overall?

If you're looking for the most enjoyable content for your money, my recommendation is to pick one of the "big" expansions, at this point either Labyrinth of Ruin or Shadow of Nerekhall.

In each of those you'll get:

-A full campaign

-Map tiles for said campaign

-4 monster types

-lieutenants

-4 heroes

-4 hero classes

-some cards (shop, travel, condition, etc.)

I found that Shadow of Nerekhall was the most enjoyable over all. Thematically this expansion really interested me and I thought that it was the most even in general. The monsters in this campaign are some of my favorites (especially the Ynfernael Hulks) and I really liked the added "corrupt citizen" and "influence" mechanics for the overlord (something I found to be lacking in the other expansions).

If my gaming group ever breaks up and I am forced to buy my own copies of the Descent games, this will certainly be the first expansion that I buy. I would definitely recommend it for when you decide to expand your Descent playing.

I would actually agree on starting with Shadows of Nerekhall. All the monsters that come with it are useful and the new classes are great and interesting. Also it's new, so it's easy to find.

The best thing I like about Nerekhall is the campaign though. Most of the quests are single encounter, so they are a bit longer than a normal "half-encounter" quest like in the starting campaign, but because you don't have to clean up and build a new map it speeds up the session time.

Go for Nerekhall, then maybe a small box expansion or a Hero/Monster pack if you want some new options for everyone.

Also you should for sure grab at least one lieutenant pack. Any will do, just get one that looks fun to you, but it adds a bit more punch to the overlord side that I think fixes a bit of balance in the game overall.

why not getting them all ?

the game is made for that !

I'm buying them in more or less chronological order, so I'll get the older ones before they're out of print. All of them have something cool you'd not wanna be without once you have it.

Thanks for the advice, everyone! Do the heroes tend to be favored in the base game?

In the base game it varies form mission to mission, for example Death On A Wing can be nearly impossible for the heroes if you lose Encounter 1. Across the whole campaign I feel its pretty even though, with maybe an edge favoring the heroes.

A lieutenant pack I think curves it nicely. Besides secret rooms and rumor cards, a lieutenant pack is the only thing that actually adds a new element to the game. The expansion are basically just "more choices," but same mechanics. Also it seemed like money was a concern for you, and the lieutenant packs are cheap. There should be another thread floating around about preference in lieutenant. Dig it up and feel free to necro it if you have questions, or ask here too, I have them all.

All of them.

All of them.

why not getting them all ?

the game is made for that !