We need Waste Management to start putting dumpsters out for people to fill.

So this is still there 4 years later? The reason illegal dumping is way up is the City's complete lack of enforcement and when waste management got he week day contact to pick up illegal dumping in the city they raised the landfill rate. People from all over the bay area come to Oakland to illegally dump zero enforcement = zero consequences. Putting dumpsters out would require waste managemento jack our already high garbage fees though the roof to compensate.

Can't folks request bulk waste pick-ups once/twice a year. Is it difficult?

People do this all the time. But there are the lazy or uninformed. Plus this time of month is eviction dumping either the evicted tenant or landlords haul there unwanted junk to the curb knowing there is little chance of being busted. Since the City of Oakland refuse's to keep its residents up on the rules and has a zero enforcement policy this epidemic will continue at the tax and rate payers expense.