Maybe you can point me to some literature to read regarding that aspect of speaker design. the same goes for other aspects as well.
Try
diysubwoofers.org. (The theories & physics for a subwoofer are the same as a regular woofer.)
You could try looking for a speaker design book at Amazon.com or
Parts Express. I can't recommend a specific book... I've got a pretty good book, but it's way outdated (before software made things easier), and I've got another book that has several "cookbook" designs, but not enough "theory".
Playing around with the software should help too. i.e. You can easily plug-in some different port dimensions, or try a sealed box to see what happens to the response curve...
Assuming I am using the term 'vent' correctly. Any links to design literature would be great.
Yes. The terms "vent" and "port" are interchangable. (Maybe there's some technical difference... in either case we're talking about a "hole".)

I notice that the cylinder for the mid-range is used to open the back of the mid range to the outside of the cabinet. Any comments on this? Is this a useful feature or marketing?
It's unusual, but it's something like the Bose
Direct-Reflecting speakers, designed to reflect some sound off the walls to give a sense of space... From
RadioShack.com:
The back portion of the midrange element is left open to radiate sound to
the room rather than absorb within the system or element enclosure. This
allows an increase in spaciousness to the sound which contributes to the
life-like sound quality of Realistic Optimus-50.
The effectiveness of something like that will depend on the acoustics of the room, placement in the room, etc. Again, you can experiment with plugging-up the midrange "port".
Any ideas on how to assess the condition of the tweeter, mid-range...?
If the midrange and tweeter are not physically damaged, if you're getting sound out of them, and if the sound is OK*, they are probably fine. (I assume that your woofers are either physically damaged or the foam surround has rotted-away.... Woofers with rubber or cloth surround can last "forever", but foam seems to deteriorate.)
... and electronics?
The electronics are probably in good shape. Assuming nothing drastic like corrosion... Coils last forever. Resistors (if any) last forever. Most "film" capacitors last forever.
However, your crossover may use
non-polarized electrolytic capacitors, and they can change in value (microfarads) as they age. Electrolytics are cheaper and they have looser tolerances than other capacitors.
Electrolytic capacitors have sort-of a crimp around each end, and a shrunk-on plastic insulating wrapper. A
film capacitor (or other non-electrolytic) will usually have a smoother, "cleaner", appearance. If your crossover uses something other than electrolytic capacitors, that's a sign of a good-qualtity speaker system.
If you have electrolytics and you decide to change them, just get the same value (uF) and the same or higher voltage. If you get an electrolytic, make sure to get a non-polarized electrolytic. (Most electrolytics are polarized... Non-polarized electrolytics are special and only used in crossovers.) If you upgrade to non-electrolytics, they will be larger and it might take some creativity to install. You probably won't
hear a difference if you replace the capacitors, but it wouldn't hurt. (I'm assuming you have a soldering iron.)
Your speakers also have mid & tweeter level controls. These can get "dirty", and might have dead spots. If these are not operating "smoothly", you can spray some
Tuner/Control Cleaner into the controls and work them back-and-forth. That usually makes the controls "good as new".
* You'll probably have to replace the woofers before you can really evaluate the sound quality of the mid & tweeter.