This is a very broad subject to start with and involves a lot of parameters and much discussion.
The first thing I would suggest is to get with your bearing suppliers and get some literature about analyzing bearing failures to get you started. All manufacturers have some information. Ask for literature on bearings in general so that you will be familiar with all the parameters in the use of bearings. There is a lot of misunderstanding concerning bearings and their operation.
But the general consensus is that bearings start failing from the following reasons, one, two, or all.
Lack of or improper lubrication.
Installation
Overload
Wrong bearing selection
Enviroment
These are just a few of many.
I’ve found out that in the majority of bearing failures lubrication plays a major role and in many cases is the root cause of the failure. Unless there is a smoking gun that points to failure mode of an inservice failure of bearing that has been performing well over time I will try to test the same bearing with a different lubricant.
It is a lot easier to monitor bearings than to analyze bearing failures. A bearing removed prior to catastrophic failure will yield a lot more information than a basket case.