Some Di2 connections are recessed and super awkward and are not easy to plug or unplug even with the tool (Drop bar shifters, front mech), with the usual result being chewing the plastic body of the plug. Some have good access and can be done (with care) with your bare hands (rear mech, internal battery). Junction A and B fall somewhere in between, depending a lot on if other connectors are in the way.
The connector itself is just a standard MCX RF connector in reverse (ie the Di2 plug is female MCX, socket is male) and I’d expect it to be robust to repeated connects / disconnects, within reason.