The present technology is generally directed to spinal cord modulation leads having one or more sidewall openings configured for inserting stylets to steer and/or position the leads within a patient and/or with respect to a pulse generator, and associated systems and methods. In some embodiments, sidewall opening is generally positioned in an intermediate portion of the lead and is operatively coupled to a lumen extending distally to a distal end of the lead, and/or proximally to a proximal end of the lead.