He cut through a layer of insulation to access the roof cavity directly above the Woolworths store.
Wheeler then removed a section of roof panelling to give him direct access above aisle 18.
He fastened a green ratchet strap to a metal beam within the roof cavity and threw the end of the strap down to the Woolworths floor, then used it to climb down himself.
Wheeler used a metal bar to pry open a locked cupboard and take approximately 46 cartons of cigarettes, worth over $26,000.
He placed the cigarette cartons inside a doona cover and left the store through an emergency exit.
Eight days later, Wheeler robbed a Caltex service station in Albion Park just before 3.30am, cutting several wires to disable the alarm box.
He used two screwdrivers to force open a cabinet door and obtain several sets of keys, which he then used to open a cigarette cabinet.
He loaded almost $13,000 worth of cigarettes into a large green and white bedsheet, before grabbing a V energy drink from the fridge and leaving the store.
Police said he was only on the property for a total of six minutes.
He was arrested on April 30, 2021, after a warrant was issued for his arrest.
Defence lawyer Matthew Ward said Wheeler struggled with his mental health, gambling and substance addiction, and was willing to attend rehabilitation.
“This is not someone seeking to obtain great profit,” Mr Ward said.
“It’s out of desperation in some respects.”
Magistrate Girotto handed Wheeler a 26-month aggregate sentence, with a non-parole period of 13 months backdated from April 30, 2021.
“You’ve certainly got some skills if you can do what you did in these matters,” Magistrate Claire Girotto said.