Do updates with '.' always require reboot?
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The first update for 2.3 was 2.3_1, which required no reboot. The second update, to 2.3.1, required a reboot.
Do all updates with a '.' require reboot?
Yes. Think of it as 2.3.0_1 and 2.3.1. There may be a 2.3.1_1, in which case you may or may not need a reboot. 2.3.2 will.
Here is a comment by cmb about noting which upgrades will or will not need reboots: https://www.reddit.com/r/PFSENSE/comments/4jz1fb/231release_now_available/d3dmniu