Playing Skyrim regret-free

Question

What's amazing about these open world games is the freedom I have as a player. If I don't want to follow the main story line for a while, and just explore, I can do that, and the game won't break.

OTOH, I don't particularly like the feeling of having made a significant, bad choice in the game, among the lines of Yeah, that dialog option you selected hours ago? This amazing quest line is now off limits.

IIRC, in Morrowind, I had to progress through a few different guilds' quests in the right order, otherwise it'd have stopped my progress in a few guilds.

As a Skyrim example, it doesn't appear that the very first choice made in Helgen at the very beginning has much significance. If someone told me It's not that significant, you still get to choose sides (or, rather not told me "This is important"), that'd help.

Another example: Based on a question I read here, I should probably make sure that I don't throw away any of the dragon priest masks and need to make sure to collect one during a specific quest. This would be relevant for this topic if I could easily miss it otherwise while doing that question.

This includes accidental problems possibly caused by bugs: It appears it's easily possible to lose the option to buy one or more of the houses due to bugs, and one needs to be careful about the order of playing through some quests.

It doesn't matter too much which of the love triangle guys in Riverwood I support: That's not nearly significant enough.

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Are there non-obvious, hidden decision points in the quests and story lines? When playing in a certain area, doing a certain quest, what do I need to make sure to do or not do, to not accidentally prevent me from getting or achieving something significant?

I still want to explore on my own, but want to be aware of which choices are important.

This is somewhat related to that question.

Answer 1

The only major example of this that I can think of is that there is a segment of the main quest that is skipped if you resolve the Civil War prior to reaching it.

Similarly, your decisions during that chunk of the main quest can allow you to skip some of the more repetitive fort-conquests during the civil war if you play your cards right.

Other than that, and the obvious mutually exclusive choices (Stormcloak/Imperial, Blades/Greybeards), there shouldn't be any other dead ends.

Answer 2

I'm not aware of any major problems you can run into.

Most decisions with big results are fairly obvious, in some cases you even get told explicitly that a decision is final (and even then there are occasional "outs" that might help overturn the decision).

But some quests are broken in that finding the item-to-be-tretrieved before getting the quest can prevent you from finishing the quest.

Disclaimer: I don't tend to go on random killing sprees, so I can't speak on the effect of those on sidequests: their quest-givers might not be marked as essential and you could easily lock yourself out of some sidequests by doing that. The people essential to the main quests are essential and you can't kill them anyway.

Answer 3

You can choose to kill off the dark brotherhood and not being able to join them. That's the only one I know.

Answer 4

The UESP wiki, 'Quest Timing' article has a detailed list of quests (and notes about those quests) that will have a significant impact on other quests and the game, in general. Some of them are due to bugs, and some are because they are designed to be that way.

It also recommends if a quest has to be done early or be postponed before/until another quest has been finished or another game event has happened, to prevent bugs or a negative impact on other quests, or the game.