Where do you all suggest that I go after playing the base set? I would have liked to play in chronological order, but it seems that the first cycle is rarely ever in print. So where should I go? I am afraid that if I randomly pick an adventure pack the cards won't be powerful enough to work.

Don't randomly pick an adventure pack, because you need to have the deluxe that goes with it to play the adventure.

But if you have a cycle available to you (in stock), you can start there. All cycles have a mix of difficulty among their quests, and your lesser pool may indeed have trouble with the tougher quests, even in easy mode. But there's no shame in using easy mode, especially with a limited card pool. I think you can start anywhere and still succeed.

If you scroll down this page (https://www.fantasyflightgames.com/en/upcoming/), syrillian, you'll see that the vast majority of the first 4 cycles (Mirkwood, Khazad-Dum/Dwarrowdelf, Against the Shadow and Ringmaker) are either currently at the printer, or already on the boat... so they should hopefully be in stores in the not too distant future.

I think you'd be fine with just about any of the cycles you can find. The only one I think you might have trouble with is Heirs of Numenor / Against the Shadow, where they frontloaded all of the difficult quests rather than having them at the end of the cycle.

If you can find them, the Saga expansions make a good choice too since they're kind of an independent cycle in and of themselves (they follow the storyline of the books).

This is what you're looking for:
https://talesfromthecards.wordpress.com/2013/09/13/new-player-buying-guide/

Buy Deluxes first, thats my plan

Haing gone through this already my experiance has definitly brought to a few conclusions.

First, One Core set is really enough unless you plan to have more than 2 players. Yeah there is something to be said about having a wider card pool, but it really didnt add that much to the game for me you. Its the one thing I feel is skippable.

Next are the cycles. In my humble opinion The Shadows Of Mirkwood has been a lot of fun and quite challenging for a newbie. Its "less complex" rules wise, I noted that a lot of the other cycles become a lot more complex with more things to track.

The Deluxe Expansions are always worth getting. Its 3 quests and lots of cards, in terms of value for money, you get a lot more out of these and having them gives you the freedom to purchase from any of the cycles in any order, so getting Deluxe Expansions as they become available is always worth it regardless of order.

The best thing I got into though has been the Saga Expansions. There extremely thematic, challenging, filled with great cards and campaign mode is an added bonus that has so far been among my favorite ways to enjoy the game. That said, you do need some cards from other sets, other wise these can be quite tough. Also, while they are sequential, they like Deluxe Expansions aren't reliant on anything and are well worth getting even if you don't have them sequential and I would probobly recommend buying them based on availability.

In terms of the rest of the expansions, personally I have found a lot of the print on demand/ Gencon special stuff to be super fun. Murder at the Prancy Pony is one of my favorites, probobly have played that one more times then any other, but so far pretty all of the ones I have gotten have been really good. Only bad part with them is they don't come with any player cards (its just the quest stuff), at least the ones I have gotten so far.

Cycle wise, I think its mostly about flavor, I'm sure there are plenty of opinions about which cycle is best, or which has the best cards, but so far for me personally I have not run across anything that is outright bad or not recommended. I have my favorites of course, usually based more on theme than anything but again remember you have to have the Deluxe Expansion to play expansions in a cycle.

Don't know if that helps, I guess I'm a bit of a fan boy even after owning the game for quite a while now, but I think the reason I like the game so much is because I havent run across anything bad yet. Challenging.. definitly, but bad.. not so much.