Not loading playthrough states

Is the game connected to the Dragon Age servers? It won't upload if it's not.
Unsure how often the game uploads data to the keep, but if you haven't gotten very far, you might want to keep going for a while, see if that's the reason. How far along are you? 

What inconsistencies have you noticed, by the way? Just curious. Some things have been made canon (such as Leliana being alive, just as Anders was alive & a warden in DA2 despite you being able to turn him over to the Templars in Awakening) regardless of previous choices (Leliana does get a pretty good story out of the whole "that * Warden tried to kill me!" thing). 

It is connected to the servers, that I made sure of as well, or at least I'm pretty sure; how would I verify that?
I am only an hour or so in, maybe a few hours, so that may be the issue.

The only inconsistency I've encountered so far is that Threnn says that Queen Anora lent her to the Inquisition, despite me making Alistair King without him marrying Anora.

OK, the game does respect your choice regarding who rules Fereldan/the fate of Alistair, so it seems your world state is wrong.

I'd check back with the playable states after doing the main quest with either the Mages or Templars, as I know that's a tile in the Keep, and I think it's the first important decision you make, so it'd make sense to do the first upload then. Although saying that, my Keep makes playthrough states for characters I start creating and cancel (have had a few where I've forgotten to change the gender or something, or changed my mind, etc), so maybe yours is being problematic... Anyway, if it doesn't upload after that quest, I'd get on to EA for help. Unless you don't want to continue your game with the wrong Keep file, as many other things could be wrong, and it's early enough to restart.

As far as I'm aware, the main menu tells you when you're not logged in, and provides a convenient button to log in (I've only not been logged in on occasions where my internet has dropped out while I'm playing).

To make the game use a world state from the Keep:

1. Create the world state in the Keep (on the website)

2. Sync that world state. (also done on the website.)

3. Open and log in to Orin, making sure it is in ONLINE mode.

3. Launch the game.

4. Log in to the game.

5. Begin a new game.

6. Choose custom world state.

7. Stay logged in until you have control of your character.

That should lock your world state to that game so long as you don't edit and/or re sync from the keep again. Syncing form the Keep again will change the world state of your current game.

That's the first I've heard of resyncing world states affecting the current playthrough (since the world state data is saved in your save file, you'd think that would take quite a bit of doing).

Well, I got up to the Mage/Templar quest line, still no current playthrough and I also tried those instructions to a T and it still did not show up as my custom world state in Inquisition.

OK, I think it might be time to take it up with EA, @Baedon_Lykos. You can contact them here (you might need to change your country/language settings). Just have a list or something handy of everything you've already tried to fix/diagnose the problem, so you can skip the whole 'they're telling me things I've already done' parts. Sorry we couldn't be more help. 
If you do find a fix, please come back and let us know, it might help someone with the same issue in future. 🙂

So I finally figured out what was happening; apparently my girlfriend ha switched to her Origin account on my computer before I even downloaded the game and I never noticed, so the World states I was making was for a different account that the one for the game I downloaded, so issue solved there.

However, hitting another issue and I'm not sure if I need to start another thread for this, but I recently opened up the Emprise du Lion area, did a few quests and then went back to Skyhold to empty my inventory; afterward I went and did a couple of side-quests in other areas, no problem. However, whenever I try to go back to Emprise du Lion, the game crashes whenever I get into about the center of town; been to Forbidden Oasis, Skyhold, and Storm Coast, just to see if it was the game at large or just that one area and haven't encountered any other problems; any idea on what the issue is and/or if theres a fix?

@Baedon_Lykos Think you'd be better off starting a new thread for that issue, totally separate issue. Glad you did figure out your other issue (why do we never think to check such simple solutions/potential causes first? 😛 ) 🙂