Installing HP Laserjet P1102 Printer

Another solution is to install the printer on the local workstation and then map the driver to the printer IP address on the network. HP claims to have a Windows 8.1 driver for the P1102 printer.

http://support.hp.com/us-en/drivers/selfservice/HP-LaserJet-P1100-Printer-series/4110394/model/4110303

You might have better performance with a printer that has a PCL-based driver.  The HP LaserJet P1102 uses a host based driver.  Printers that use "host based" drivers have very little processing power of their own, so the bulk of the print job is processed on the computer "hosting" the printer.  Host-based print jobs are larger & take up more system resources.  They are really designed for small office or home use and aren't recommended for a network print server.

But, even so, a direct connection using USB should work.  I don't think the P1102 has built in network connection: you can only connect it using Wifi or USB.

If you log on to the 2008 server, can you print to it?  Can any other PCs print to it?  I would install the 32 bit drivers on the server as trgrassijr55 suggested.

You bought the cheapest printer available, so sadly you have this problem now.
On older Windows versions, the XPS driver update solved this problem, but as you can see on the official driver download page, it stops with Windows 7.
The question is now, do you dare install that (both on the server and on the client) and try to make it work with Win8.1 (as I never needed it to test in this situation I can only tell you it works in an Win2003/XP environment)?

Kimputer,
I saw XPS drivers for Server 2008 for this printer on HP's site.  The driver download links all appear to be the same no matter which version of Windows you select (either WinXP, Vista, 7 & 8 or Server 2003/2008):
http://ftp.hp.com/pub/softlib/software12/COL32622/bi-83979-5/LJP1100-P1560-P1600-XPS-win64-en.exe
http://ftp.hp.com/pub/softlib/software12/COL32576/bi-83891-5/LJP1100-P1560-P1600-XPS-win32-en.exe

Although, I do agree with your assessment in general: this lower end printer is not designed for use on a print server.  Things would no doubt work much better if a higher end, PCL-compatible printer were in use, however, it doesn't mean you can't get this set up to work.

This technet article describes how to drivers to the print server for 32 or 64 bit client PCs:
https://technet.microsoft.com/en-us/library/cc732946.aspx

Thanks for the input it was really helpful.