ContactTower
Totally agree 1000 feet is a good margin to use.
Being a realist pilot will use smaller margins sometimes much smaller and there lies the danger.
Normally if you fly an approved approach for a cloudbreak to a VFR field then that usually means a normal cloudbreak is not possible!
Transitioning from IFR IMC to VFR minimal VMC is always confusinng meaning getting your mindset into a VFR gear.
If when you break out the pilot is not secure I would recommend a landing request or a predeclared intention to land if VFR not acceptable to the pilot!
Obviously familiarity with the area plays a large part in that decision
Pace