A system comprising: an aerial vehicle (100, 200, 500); a sensor coupled to the aerial vehicle; a winch system coupled to the aerial vehicle, wherein the winch system comprises a tether disposed on a spool, a motor operable to apply a torque to the tether, and a payload coupling apparatus (226, 512, 700, 1000) coupled to a leading end of the tether and configured to mechanically couple to a payload (228, 508); a repositioning apparatus configured to reposition the payload coupling apparatus in at least a horizontal direction; and a control system (208, 210) configured to: identify the payload to be picked up by the aerial vehicle within an environment; control the aerial vehicle to hover above the payload; and control the winch system to deploy the payload coupling apparatus by unwinding the tether from the spool; characterized in that the repositioning apparatus comprises wheels (604, 704) coupled to the payload coupling apparatus and driven by additional corresponding motors; and in that the control system is further configured to: control a position of the aerial vehicle in coordination with the winch system to deposit the payload coupling apparatus and the wheels thereof onto a surface in the environment near the payload; and while the aerial vehicle hovers above the payload: (i) receive, from the sensor, sensor data indicative of a position of the payload coupling apparatus in relation to the payload and (ii) reposition, using the repositioning apparatus and based on the sensor data, the payload coupling apparatus in the horizontal direction to mechanically couple to the payload. an aerial vehicle (100, 200, 500); a sensor coupled to the aerial vehicle; a winch system coupled to the aerial vehicle, wherein the winch system comprises a tether disposed on a spool, a motor operable to apply a torque to the tether, and a payload coupling apparatus (226, 512, 700, 1000) coupled to a leading end of the tether and configured to mechanically couple to a payload (228, 508); a repositioning apparatus configured to reposition the payload coupling apparatus in at least a horizontal direction; and a control system (208, 210) configured to: identify the payload to be picked up by the aerial vehicle within an environment; control the aerial vehicle to hover above the payload; and control the winch system to deploy the payload coupling apparatus by unwinding the tether from the spool; characterized in that the repositioning apparatus comprises wheels (604, 704) coupled to the payload coupling apparatus and driven by additional corresponding motors; and in that the control system is further configured to: control a position of the aerial vehicle in coordination with the winch system to deposit the payload coupling apparatus and the wheels thereof onto a surface in the environment near the payload; and while the aerial vehicle hovers above the payload: (i) receive, from the sensor, sensor data indicative of a position of the payload coupling apparatus in relation to the payload and (ii) reposition, using the repositioning apparatus and based on the sensor data, the payload coupling apparatus in the horizontal direction to mechanically couple to the payload. identify the payload to be picked up by the aerial vehicle within an environment; control the aerial vehicle to hover above the payload; and control the winch system to deploy the payload coupling apparatus by unwinding the tether from the spool; characterized in that the repositioning apparatus comprises wheels (604, 704) coupled to the payload coupling apparatus and driven by additional corresponding motors; and in that the control system is further configured to: control a position of the aerial vehicle in coordination with the winch system to deposit the payload coupling apparatus and the wheels thereof onto a surface in the environment near the payload; and while the aerial vehicle hovers above the payload: (i) receive, from the sensor, sensor data indicative of a position of the payload coupling apparatus in relation to the payload and (ii) reposition, using the repositioning apparatus and based on the sensor data, the payload coupling apparatus in the horizontal direction to mechanically couple to the payload. control a position of the aerial vehicle in coordination with the winch system to deposit the payload coupling apparatus and the wheels thereof onto a surface in the environment near the payload; and while the aerial vehicle hovers above the payload: (i) receive, from the sensor, sensor data indicative of a position of the payload coupling apparatus in relation to the payload and (ii) reposition, using the repositioning apparatus and based on the sensor data, the payload coupling apparatus in the horizontal direction to mechanically couple to the payload.