I'd argue it's still a strong objection, your solutions require a lot more bureaucracy and would still be filled with loopholes.

A couple quick ones:

1. Registering the car in your grandparents name, who have no income, to avoid tolls. Or perhaps your stay at home spouse (assuming you file separately).

2. Make your next vehicle a light truck or van to avoid potentially hundreds in monthly congestion tolls. Luxury trucks are very much a thing.

I agree your plan would technically work, but it would be filled with exceptions, loopholes, and political handouts. That is rather fitting for NYC though.