About SegWit -> We need to implement native segwit address parsing. About half the explorer support it and there is a node package that has support for it. Maybe we can try to implement it in Insight.
Mostly. They can submit a Pull Request to include their pool tag in our explorer. We also need to upgrade the production code to the latest one. This should be done by Sysops.
About Bech32: Actually newer version of the Insight explorer already has good support. However they also changed their api A LOT. It means that a āfull upgradeā may break our existing clients. A better way is to run both the old and the new explorers together and tell the people to migrate in a transition period.
BTW I think this thread can be moved to a public category.