Warning: Disable "Use RAM Disks" before upgrading
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I have been beating my head against this nightmare for months, ever since I accidentally got stuck on the 2.3.5 branch. On anything after 2.3.4, you MUST disable "Use RAM Disks" in System->Advanced->Misc.
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If you don't uncheck this you will see transient or permanent failures of pkg to run at all.
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You will (eventually) get stuck on this permanently: ERROR: It was not possible to identify which pfSense kernel is installed
At that point, you can never upgrade again. I lost three days to catastrophic data loss resulting from trying to repair this mess before I finally figured out it was the (*@#$ RAM disks. pfSense used to be reliable. This has become a nightmare in the last couple releases.
You have been warned.
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I've been using RAM disks since day one with pfSense, never had any issues. Them again, when I do a major update I use an image file install and then reload the config, or now I load the config when the image is installing.
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I run a couple systems here with RAM disks and they seem to be OK.
Though you do need to make sure they are properly sized. If they are small, then things can break badly.
RAM Disk handling has been improved quite a bit on 2.4 since we dropped NanoBSD.