I’ve been avoiding upgrading my Hassio due to the fact that I did not have much luck in my last attempt (I was not able to upgrade to 0.101.3 - if I remember correctly, it was due to the changes in the authentication).
As I am further and further apart from the latest release, I want to give it a second try, but I do not want to break things, specially during the coronavirus lockdown 
Any immediate advise regading this upgrade that you may want to share with me?
If you had problems with authentication, solve that first.
Then read all breaking changes between 0.97.2 and 107.7, and solve them one by one.
Personally I feel the same as you. Probably an unpopular opinion, unless there are new features you plan on using or something that isn’t particularly working I wouldn’t update. I keep telling myself not to update but when I finally get everything working I usually do, and then things break.
If you do upgrade, seeing as this would be a big one, I would expect that you’ll have plenty of fixing to do after.
I did go for the upgrade. Surprisingly it was done better than I thought it would be, as my hassio booted properly without any major difficulties.
I had to do some changes on my configuration files, namely the Google Assistant integration, as well as some devices that are using the wake on Lan feature.
I was using groups with views to organize my devices and sensors, but views are deprecated now, so I will have to learn lovelace in order to keep things tidy on my hassio.
Nonetheless, I still have some things to sort out, namely the webostv integration that does not seem to be working.
I am also having some trouble with the zwave refresh_entity that I am using to update my fgrm-223 percentage status. I am getting the following error:
Error executing script. Service not found for call_service at pos 2: Unable to find service zwave/refresh_entity