The only time I would use an insulated connector is if its a female spade and the insulation goes over the connector. Every other common connector (ring, fork, ****) I would use marine heat shrink with the glue.
I can see a use case for ratcheting crimpers for production work. They likely are faster and more accurate, but they seem quite bulky to me so for any service work I'd go for pliers since they're easier to get into assembled and tightly packed areas (hvac work, automotive etc). I've never had issues with a quality Klein or channellock plier crimp.