Ha, funny, this is what I do for a living, kind of. I program backends and databases for spatial applications, so I try to stay up on the tech.
I would simple Check with NYC and see if they have a map such as that. My hometown of Thunder Bay has maps like that on their site and is a fraction of the size of NYC, they use an ArcIMS Server running Onpoint. I'll check for you.
NYC Subway website isn't that great is it?
http://www.mta.nyc.ny.us/nyct/maps/submap.htm
Wikipedia has some decent links
http://en.wikipedia.org/wiki/New_York_City_Subway
An example of a googlemaps mashup, zoom in, out, pan
http://www.onnyturf.com/subwaymap.php
take a screenshot and print it, hehe
As for parking, I'm sure there is something out there along the same lines, is that something you can use?
Otherwise, if you got me the data I could do it for ya =), but I only have Canada sorry.
But seriously, this almost deserves its own thread, but you can check out other people's mashups (putting APIs on your own site, such as GoogleMaps). One of the best listings for mashups is over here:
http://programmableweb.com/