I guess to me it just seems like you want to deter end users picking taxis/ubers over trains a bit more, and $1-2 is not going to do that when they are already paying 5-10x subway fare for their ride.
I can see by your example how over the course of the day the taxi/uber collects a lot of CPZ fees for the city, I just don't see the fee reducing anyone at the margin from using taxi/uber.
At the end of the day I'd love to see transit improve, and if all this does is reduce traffic for the well heeled who already are taking taxi/ubers.. I mean I win there too, but it doesn't feel great.
For the record when I commute it's always by transit, the problem is weekend/night service has degraded to the point that I feel forced to take taxi/uber quite often. I've lived in NYC nearly 20 years and have found, if anything, night/weekend service to be less predictable and more perplexing. This again harms the less well off even more, as they are more likely to be doing shift work / non-traditional workdays than your M-F 9-5er.
Just this weekend, yet again, I was trying to get around midtown and Apple kept telling me what should be a 6min trip would take 30min by train even though I was 5 seconds from subway entrance. I couldn't understand why, and went to MTA website and saw no alerts for the 6th ave line. Then I went to the live train time page and realized the problem - the 6th Ave line was running at 15min headways, so Apple had me walking 2 blocks to 8th Ave then to wait 15min for the train (possibly 30min if its a B/D and I needed an F/M). This was Saturday around dinner time. Just awful service.