Glad to help if I can...
perhaps you're juggling too many unknowns as you try to diagnose your problem?
The first thing I'd do if I were having this problem - assuming that you haven't already done so - is to boot the Compaq from a DOS floppy or some old diagnostic floppy and make sure that you can access and use the printer in that simplest of all worlds. If Compaq do things in a more or less reasonable way you should be able to ascertain the IO port and interrupt associated with the parallel port from the bios setup.
Once you've verified that the printer and cable and the parallel port all work correctly then you can quickly go on to seeing if you can print directly from e-smith ...
and then once that works you can look look at what windows and the various network bits and pieces are doing, etc. Ordinarily the lpt1: IO port and IRQ shouldn't be issues unless yours are weirdly non-standard or you have inadvertantly done something while trying to solve the problem that has caused linux to be confused.
I hope this doesn't come across like I'm lecturing at you - it's just that there are so many variable that unless some are eliminated it will be really confusing to try to assist via messages.
Once you're happy that you can access the printer from the PC and that you can print from Linux I can take you step by step through what is required to connect from a Windows machine on my system if that will help (we run both Win2k and WinMe so we go from the ridiculous to the slime

.
I'll check back and see how you're going. Good luck.