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There are multiple quest mods that I don't plan on playing through until level 20-ish. These mods are completely separate from the vanilla Skyrim quests.

Would installing them later cause conflicts? Should I install them before I make a new character?

Some of these mods include Summerset Isles, Falskaar, Undeath, and The Wheel of Lull.

Another mod I am looking at is Helgan Reborn. The mod pages indicates that I should not install it at the beginning of a new game, but rather only after a specific condition has met. For these mods, should I install them ASAP?

5

I would say that install all the mods before starting a new game, except the ones who specifically say that you should install them at different point, like that Helgan reborn. Check out the respective mod readme and/or instruction files to ensure functionality. It is always a slight gamble if the mod functions correctly. Some mods may not even function if you do not start a new game to begin with them.

3

It's usually safest to install mods before you start playing on your character, but it's generally safe to install mods mid-playthrough as well. It will highly depend on the mod itself and reading the mod author's installation instructions is always important. Try to follow them.

In some cases, you cannot access a required piece of vanilla content due to a mod overwriting it, so you'll need to do that first in vanilla. But cases like that are rare and often caused by poor mod design.

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