One approach to this kind of problem is to use Ghostscript as a raster image processor on the PC to drive the old printer. This depends on having a recent installation of Ghostscript, as well as Redmon which is a generic tool that can make an ordinary application appear to be a printer port to Windows.
In addition to turning an old printer into a postscript compatible printer, Ghostscript can also produce high-quality PDF files, and with a suitable Redmon configuration can be used to make a print-to-PDF solution.
A trick I've found handy on occasion is to set it up to write TIFF or PNG files with Redmon to get a print-to-PNG printer.
Unfortunately, redmon isn't quite ready for 64-bit windows. According to its site, the authors are planning for a beta release that includes a 64-bit compatible build in June 2009, which if you are keeping score, is this month....
Google provided some hints that others are thinking about this issue, and there may be one or more 64-bit builds of redmon available from alternate sources.