Jacob

Agree on both the PSU and SD card items. I run pi PSU via a lipo battery bank as UPS, so I would not suspect that.
As far as the SD card is concerned, I had similar problems about 6 months ago, and built a new image on a new SD card. The old one was 2 years 3 months old.
My Pi has the 3 Alu cooler fins on, so despite this, does run in the 45 - 55 range. maybe i should add a fan.

I found my Raspberry Pi to be a bit unreliable when it gets hot.   I bought an aluminium case with better ventilation holes from the Pi Shop, removed the silly (and airflow impeding) reset hat from the top of the motherboard and added a very small fan to keep it cool.
It seldom goes over 36 C nowadays, and it's very stable whilst runing ICC v2.9.7...

It could also be a micro SD card on the way out. They have a finite amount of read/write cycles. The timeline you are describing points to the SD card as the most likely suspect.

Hi @Jacob,
I'm on 2.8.8, and also can report less than 100% reliability. Had to kill ICC a few times over the last few weeks.
I must mention that i do suffer from unreliable Internet at times, but i didn't think that would influence things.
Maybe time to upgrade to the latest version 2.9.7, as 2.8 is no longer supported. Needs a new image and machine registration. I will try that in the near future, time permitting.
I always wait a few weeks before upgrading, in case a few bugs crops up and needed to be sorted.