No Stupid Questions

Wolverine's healing abilities have been all over the map, but I'd wager with modern writing he'd likely be able to regrow his bones just fine. There's an article on some of his feats here. I'll mention that his chopped off hand in Age Of Apocalypse has been justified as a special case in a few ways by comic nerds (he didn't have time to wait for it to regrow, and the laser blast melted his metal skeleton to cap off the underlying bone are two common suggestions) along with the fact that Wolverine's powers have been increased by writers over time and that means he's gotten more over the top since the 90s.

It all depends on the writer whims really, but I doubt any writer would leave Logan clawless for too long. The bone claws themselves are a retcon after Magneto sucked all the metal out of Logan's skeleton in the 90s anyway, which shows how important they are for the character.

His regeneration factor is the reason they were able to coat his bones in adamantium to begin with, and yes; he has been depicted as being able to use bone claws before that happened. It really depends on what medium and timeline. Marvel does a lot of alternate realities, plus all the various movies that existed before the official MCU.

As already covered, he has bone claws after magneto pulled the adamantium from him.

During the comics afterwards, his claws got stomped (iirc by sabertooth), and broken in half.

They regrew fairly quickly, but were deformed for a while. Lost track of that run, but they eventually got put back to his normal.

Overall, Wolvie can regrow anything except the adamantium, and even that isn't off the table since if he had a source for it, his power could conceivably use it to reproduce what was there.

Fwiw, he's been blown up to the point he was nothing but the adamantium and some random bits, then recovered (iirc it was in the MAX days during a crossover with punisher, and daredevil . Might have been someone else involved too, can't recall.

Last I read anything, his healing factor was essentially able to start from a single cell. As long as there's something left, he'll heal. Not quite lobo level where a cell isn't necessary, but I expect something will happen where it gets turned into that at least temporarily. Deadpool is more or less at that level as well; he came back from being burnt to ashes by a lightning strike. So there's precedent for healing factors the go beyond cellular activity alone

...what happens if he gets cut in half, perfectly midline/saggital and the two halves are separated so they can't just heal back into eachother?

Does each side heal into a separate whole Wolverine?

You could pin his left side down onto some kind of reciprocating base that moves adjacent to a razor or saw, and just time the back and forth motion to correlate with his regeneration.

Basically a deli meat cutter, but used to print an army of Logans. Or a literal deli meat slicer depending on how you plan on using the Logans.

Have the comics/movies tackled this yet?

Yes.

He was also still an incredibly strong fighter and had his enhanced senses. I have an arc in my collection where he fought Cyber for a few issues, a villain whose skin itself was made of adamantium.

They would grow back i reckon

The claws were added, they weren't part of the original skeleton.

Not at all well versed in the comics – but he would have certainly broken a bone or gotten his skull bashed in prior to magic metal.