I agree with your concerns; in my particular case, all peripheral connections to the PC are USB. I don't require any GPIB or parallel port interfaces. For some OTHER applications, I do use external USB to serial port converters (readily available, as are I think USB-parallel port and USB-GPIB). Because of the number of USB ports (limited on the old XP boxes) I generally use external "universal" port replicators that provide lots of USB ports, an additional Ethernet port, and (most important) another monitor port for dual-monitor configurations. These are dedicated setups used primarily for QA SW testing, not production HW testing.
Actually, you might be surprised -- if you have room for some brackets. My Asrock micro-ATX Motherboard has on-board connectors for serial and parallel ports (but not on the back panel), but unfortunately I can't use them because my 4 slots are used up (2 for video card, 1 for USB 3.0 card, and 1 for Kvaser CAN card).
For industrial use, the Foxconn H61AP motherboard has some interesting features: back panel serial port, back panel parallel port, internal connector for second serial port, and 6 PCI slots. I picked one up last year, and loaded with Windows XP and a whole bunch of PCI cards (mostly CAN cards). It's still available at Newegg for <$60
My guess is that driver support is much better for Win7-32 than Win7-64. VirtualBox has good USB pass-through support and IIRC experimental PCI pass-through support (but no parallel port pass through).
I'm pretty sure you can get parallel port PCI cards, but don't know how well they're supported by software.
My concern with moving to Win 7 for a test environment is the availibility of drivers for legacy hardware. I actually like Win 7, I'm just heasitating because of the old equipment that connects to a parallel port and uses a program that runs under DOS. I notice that new PCs don't seem to come with parallel ports.
Although I make do (we're on Office 2010 at work), I'm not a big fan of the MS ribbon interface.
I strongly recommend LibreOffice over OpenOffice; it's updated much more frequently. And LibreOffice is better than MS Office in some areas; for example, LibreOffice Writer is significantly better than MSWord for writing long technical manuals (I know, I switched from MS Office to Writer for a ~250 page manual because Word was driving me crazy. Writer wasn't perfect, but it was significantly better).
I am mystified that so many folks still subscribe to the notion that WinXP was the most stable OS, and everything after was a step in the wrong direction. I have an engineering lab FULL of WinXP PCs (some LT, some DT) that are running test benches ( vehicle simulators mostly). I can't WAIT to upgrade these all to new HW/Win7Pro because these machines are running 24/7 and are used remotely by teams all over the globe. Typically, I have to do at least a warm reboot every few days, plus a full power cycle cold reboot every week or two to keep them functioning. This is absolutely due to various driver and OS issues that cause test applications (that work fine forever on Win7) to SEEM like they are working but really aren't. I suspect the memory limitations of the 32-bit OS/HW aggravate the situation; all of the replacement machines on order will run 64-bit Win7Pro with at least 8GB RAM and i5 or better CPU. The prototype one I have just keeps on keepin' on!
I have a legal secretary friend who was dreading the conversion from Wordperfect to MS Word 2007 in her office. She was afraid that she would be left behind the younger secretaries who were already familiar with it. She was actually relieved when they went to Word 2010 instead, because that put them all in the same boat.
Upgrades are a fact of life. Companies and people need to plan for them. That plan might be conservative or aggressive, but ignoring it is not a plan. Many companies (and people) wait until something forces them, such as hardware failure or a fatal security flaw.The result usually is a hasty and painful upgrade, not to mention an expensive one.
My own approach? I experimented with the early Win8 releases and came to the conclusion that it was a dog. I bought a new laptop a little earlier than I would have otherwise and went with a high-end Asus running Win7. Now I am tracking the news about Win9 to eventually decide whether to go with that or something else (I am also using an Android tablet more and more).
@MeasurementBlues: She's still on Office 2003 because asking her to change to a new look is painful.
It is, but... (a) the longer (more generations) you leave it, the more painful it will be for her and (b) there will come a point where someone sends her a document in a later format that she won;t be able to open ... at which time it will become your fault/problem (pick one :-)