Dumpsters need to be regulated because a company could be prone to producing more than its fair share of waste. Waste doesn't disappear once it is hauled away. It has to go somewhere and either be processed or stored. With so much concern about man's impact on the earth, it is not beyond reason to ask that companies act responsibly enough to manage their waste.
I think that as long as a business requires a dumpster and is able to pay for it the city should allow them to rent it as many times as they like, if there is more demand then there are available dumpsters the city should invest in buying more dumpsters to fit the demand.
Then what is the problem? Unless, the business is using the dumpster so much that the city has no more to give to anyone else. There is an easy fix to that, get more dumpsters. Cities should want businesses to be using their dumpsters as much as they can. That is more revenue for the city. Why must elected officials make things so hard?
Cities should not limit the number of times a business can use a dumpster rental in a given year. There is nothing wrong with a business paying their money to use these containers and keeping the trash off the streets. I think it would be wrong to limit the number of times they can use them.
What cities should do is implement ways that the trash placed into dumpsters can either be renewed or converted to cleaner energy. The technology is there and has been for the past several years, so it's up to the people and their representatives to take the initiative at this point.