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I've never tried OpenBSD, but it seems to have better laptop/desktop support. Maybe I'll fire up an instance in a VM tonight and play around a bit.

Is there anything significantly different right off the bat from someone coming from the FreeBSD world?

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Only binary patches for base provided by a third party (M:Tier, where a number of OpenBSD developers work).

I haven't run FBSD in years so I can't comment but I highly recommend OBSD for laptops (obviously with supported hardware).

I set up an OBSD laptop, an ancient Dell Inspiron 8000. Based on the experience, I'd like to get a lightweight, cheap, relatively modern laptop. Any recommendations? Cheapest thinkpad I can find?

Did you read the article? Ted specifically mentioned a few laptops by name.

Thinkpad x200's are perfect in my experience and dirt cheap

X201 - swap the HD for an SSD and enjoy.

Unless you want to enjoy Bluetooth of course :)

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