I have once again been reminded that Nightcloud still isn't part of a family tree prior to Crowfeather and Breezepelt. No parents or siblings, just plopped into Windclan after the clans find the lake.
I did check the wiki and apparently Su Susann's Missing Kits had her and Gorsetail (the tom who appears only in Dawn, not the Power of Three Gorsetail with part Riverclan kits) as kits of Crowfur and Larksplash, with Webfoot and Whitetail as older siblings. This has since been retconned with Crowfur being an elder in arc 1 with no relationships (idk maybe the authors thought it was awkward for Nightcloud to pair up with a cat with the same prefix as her dad), Larksplash and Webfoot equally disconnected. TNP Gorsetail appearancing once in Dawn and a brief reference in Onestar's Confession, and Whitetail now being the daughter of Sorrelshine.
You would think that Crowfeather's Trial or Onestar's Confession would have some reference to parents/where she came from but apparently not. But for fic purposes, I would like to have a clear idea of how these cats are connected.
I think I could smush the two different Gorsetails into one character and pair up her and Whitetail as siblings (I don't think this leads to incest problems?). Webfoot works easily enough as a kit of Crowfur and Larksplash continuity-wise, them as elders in arc 1 and him as an established warrior and arc 2. Their ages and Webfoot being an elder by the Great Battle mean Nightcloud doesn't really work as a littermate, since it feels weird for her to have been born early in arc 1 (she'd have to be for Crowfur to be an elder in Forest of Secrets).
Web and Night don't work as littermates or siblings, but I think I could still write in a connection. My first thought was mentor-apprentice (since Nightcloud isn't given a mentor and both side with Muclaw in the attempted coup) but he was busy with Weaselfur in arc 2 and that gets into the age problem again. I guess Webfoot could be made into her dad but I'd have to crawl through the allegiances for a free she-cat that won't add bloodline problems (there is room for an AU where those bloodline problems are leaned into with certain families marrying into each other for clan politics but that is a thought process I'm not ready for).
So current thought: between arc 1 and 2, Nightcloud was an abandoned rogue kit he found in the territory and brought back to the clan. Webfoot doesn't end up mentoring her but they still have a close bond. Due to her rogue heritage, she develops an insecurity about being a "proper" Windclan cat that partly manifests as wanting a good Windclan mate and kits (which she wants anyways but now has a secondary reason backing it). She's a little older than Crowfeather but they're apprentices at the same time; they both have prickly personalities but get along well enough. Personality aside, he's the son of the previous deputy and not interested in anyone else, making him a good enough catch. They end up making one of those "if we don't find partners by X time, we'll get together as a couple" deals.
She's one of the last to get a warrior name in the old territory, Crow gets his on the journey to the lake, and they decide to make good on the deal. She feels ready for kits (I'm sure there's some kind of bragging rights to being the first to have a litter at the lake; tho Heathertail might have been born first?) and Crowfeather's trying to move on from Feathertail, very much rushing into it like those couples who settle down right after high school. Then the Leafpool fiasco happens and he's even more eager to prove his loyalty and not further tank his reputation; at least Nightcloud still gets a litter out of it even if her hopes for an eventually-romantic or comfortably platonic marriage have fizzled out.
Having Crow essentially two-timing both she-cats reflects poorly on him but does smooth out the timeline a little; otherwise you'd have Breezepelt being conceived after the Three but apprenticed before them as implied by The Sight (even if he was born early, it still feels awkward conceptually; plus I'm a big fan of Crowfeather making well-intentioned but questionable choices that sometimes backfire horribly).
Unrelated to the above thoughts but, as someone who leans into the traditionalist style of worldbuilding, she very much does not read as a -cloud personality. Then it's a question of if she works better as a -storm or a -flower. She's both prickly and maternal so it's a matter of which came first/was most obvious by her naming ceremy. I do like the idea of a prickly Nightflower.