Vultr allows installing from ISO, so no need to shim. I can verify that OpenBSD 5.7-stable will run with no issues. One thing to watch out for is that outgoing TCP connections to port 25 are blocked until you ask them to open it up.

"connections to port 25 are blocked until you ask them to open it up"

Thanks for that info, that seems like a fairly reasonable policy.

5.8 is still currently in development/snapshot - not for amateur users.

5.7 is the latest official release. 5.8 is due on Nov 1.

Worth noting though that if you use the release, you get no updates, security or otherwise, till the next release in 6 months.

And using -stable (release + patches) is a hassle of manually applying patches and re-compiling - no binary updates are available.

If running snapshots is not for amateurs, neither is running stable.

One can receive updates to binary packages for the current -stable release from M:Tier[0] . They also host binpatches for security vulnerabilities in base which can either be installed manually via pkg_add or automatically with their openup[1] tool.

0: https://stable.mtier.org/

1: http://www.mtier.org/index.php/solutions/apps/openup/

That's not entirely accurate. You do get updates, they're just on the patch branch. See http://www.openbsd.org/errata57.html.

Running -stable is fairly simple. If you don't want to rebuild on your DigitalOcean VPS, cut a new release after an update locally, and then apply it on your VPS. See http://www.openbsd.org/faq/faq5.html#Release. This should be fairly simple to automate (and you could even write a script that only packages up changed files if you were so inclined).

If you cannot run stable, then I'm pretty sure you should let others do your system administration for you. Stable is very easy to follow with simple instructions: http://www.openbsd.org/stable.html

If you need binaries there is always http://opensource.mtier.org/binpatchng.html

Stable will cleanly build though, where running current snapshots you could come across something temporarily broken or have to debug a tough build if doing it from source. FWIW I just built 5.7 stable and the whole process took an hour and a half for kernel + userland + xenocara with no build issues. Often for stable security patches you just have to rebuild the kernel which is 15 mins work on my older AMD server.