While descending near Banning, CA, the pilot lowered the gear after becoming aware of a popped circuit breaker. At the destination, there was an overcast with the tops at 4500 ft, so he diverted toward Burbank, CA with the gear down. The overcast extended throughout the area, so he turned back to land at Palm Springs. While en route, the left engine lost power, but reportedly, it was not feathered, nor was the electric fuel boost pump activated. The pilot stated he repositioned the fuel selectors, but he could not recall to which positions. During the attempted restart, the plane descended into the overcast. The pilot throttled back and broke out at about 1700 ft MSL. Sometime during the descent, the gear was retracted. Subsequently, the left wing struck a light pole while landing wheels-up in a street at night. The plane slid about 550 ft to a stop and began burning. The right main tank still contained an estimated 10 to 15 gallons of fuel. The other fuel tanks were at or near empty. Later, both engines were started and performed normally.