When it comes to OCI, the most severe type of service is cold weather short trip driving. If your customers are putting 5k miles on the vehicle in <3 months, they are not doing much of this type of driving. Even if they are driving short trips, they are restarting a warm engine afterwards, which is not the same thing.I know these vehicles are being driven in the utmost of severe service. Key in and floor it type of scenario.
From on oil life monitoring study by GM:
The Chicago climate is not extreme in terms of either high or low temperatures. Although some of your customers may drive the cars hard and getting the oil hot, I think you could safely extend the OCIs past 5k with a good synthetic oil. One danger of extending OCIs is that if a car is burning or leaking oil, there is a greater risk of oil starvation if the customer doesn't check the oil. Using the cheapest synthetic (Kirkland) at 5k intervals will be conservative and the frequent services will allow you to better monitor vehicles for issues. Oil starvation is the most common killer of engines. There are other issues that could be caught early as well with more frequent servicing.
As far as grade, I would favour thicker. These vehicles don't spend a lot of running time with cold engines, and Chicago doesn't experience extreme cold. A 5W30 across the board should be fine, and will provide better protection for those vehicles that are driven very hard. They may burn less oil between OCIs as well if the oil is thicker, which could help prevent an oil starvation issue.
I would use high efficiency synthetic media oil filters, replaced every 15-20k miles. It will be cheaper than changing a cheap oil filter every 5k, and will result in less engine wear. You may not plan to keep these vehicles until the engines wear out, but less wear means less oil burning, which will result in a lower chance of oil starvation (see a theme here? I don't trust your customers).
Extending air filter replacements intervals will better protect the engine through increased filtration efficiency and will save you money. Restriction gauges for the airboxes might be a reasonable investment if these vehicles will be in service for a long time yet.