I run Haiku in a VM. Can I upgrade it from within Haiku or do I have to nuke what I have and start over? I haven't done a lot of customization but enough to make it a pain to do over.
If you are on the beta release or a recent nightly image, you can just run SoftwareUpdater and it will upgrade to the most recent build on either branch.
If you are on an older (i.e. pre-2017) nightly, you can still upgrade automatically, but you'll have to manually change package repositories to do so. If you are on an older release (alpha4, etc.) then you can't upgrade at all, you'll have to reinstall.
Going forward, it will be possible to upgrade from beta1 directly into beta2, or whatever the next release is.