I would love to learn more about improving pasture and whether it is possible organically without heavy spraying and cultivating.

Succession problems tend to sneak up on you so the sooner the conversation is started the better. Include all your team of advisors and family and work through the plan step-by-step. Remember to revisit the plan yearly to revise and tweak regularly as often changes happen as the years go by. Mostly communicate, communicate, communicate.