(And I'm not sure from a driving in perspective what's actually been gained relative to me taking my own car in and parking in a garage which is what I usually do.)
The congestion charge will be between $9 and $23. For certain parts of Manhattan. During certain hours. It sounds like your problem is where you live, fundamentally, not the charge.
> a thousand dollars at that point between hotel and transportation
You do see how, from a resident's perspective, you spending more money less frequently is not a downside?
> what's actually been gained relative to me taking my own car in and parking in a garage
A reduction in space wasted to parking. Also, congestion: your car adds a car to the road. (You're also a non-professional driver in a dense urban environment.)
The things that people want to deal with the PITA of living in Manhattan over depend on volume of people. COVID and WTF killed commercial office traffic - now that it's getting dark early take a walk up 3rd Avenue in the late afternoon - the offices are empty.
So the residents don't want to deal with commuters, don't want to deal with drivers, etc. Cool. I don't want to hear about bailing people out of their $2M mortgages on 800 ft^2 apartments when the cultural, dining and entertainment that brought them to Manhattan migrates to Brooklyn and Jersey.
Real estate crashing would save NYC from itself.
If it’s that much of a hassle, for most entertainment one commutes into Manhattan for, you are fine paying the toll on an Uber. People driving themselves in and sensitive to the toll are, by definition, not adding much to the local economy.