It took me about 4 years to organise my messy insurance plans accumulated over the years. The motivation was the realisation then that I was growing older and signs of aging were creeping in.
Fortunately, my health was still generally good and I could add/drop insurance policies without issues and my increasing income allowed me to add coverage a bit here and there. It just took a lot of time to compile, create online accounts to the existing policies and call up the insurance companies directly for information, and then read up and compare across. I had to create an Excel to tabulate the details.
The most significant change is after reading up about the highly affordable Aviva Mindef insurance plans in this forum, I dropped some of my expensive and/or duplicated insurance plans. I used the saving to increase some coverages and added a few missing ones that are available at the Aviva Mindef or Aviva itself (although now I realise the latter is a bit more expensive than the market average but the coverage is good).
I will take a break from this optimisation effort for a long while unless there are some major changes e.g. integrated shield plan reviews