dualbooting is often messy because windows update can delete things required for linux to boot.
or to be more specific, it deletes grub, the bootloader.
i’ve heard you can use a different bootloader called refined to prevent this from happening, that might be worth looking into.
as for which distro, it doesn’t really matter. the only real differences between distros are the package managers and repositories (servers for application and update downloads) they use by default. if you like frequent updates, you choose one that has frequent updates, if you don’t, you don’t