Hi Doremus, that's the most detailed explanation I've read, thank you so much for that. Especially the *qualifications*. I'd never considered viewing light at all when making the proofs. I "proper proofed" a roll of 135 until the sprocket holes were invisible (under indoor incandescent lighting). All the images looked too dark, lacking highlights, except for the high-contrast backlit images. Do you think this is over-printing? Or is that a good method?
It's hard to tell but I'm pretty sure that shadow detail is there, however it's HP5+ which has a long toe, so I guess at EI 320, if I start increasing [edit: development] time, I'm essentially pushing the film. I'll try a roll at EI 200, normal dev, and another roll at EI 400, and dev for 800. The interesting thing is that digitaltruth.com has both 7.5, and 10 minutes for HP5+ in Dilution B, 20C. I'll try 10 minutes first, and see if it's overshooting.
Take a look at the negative itself. If there is a lot of shadow detail that is not printing at your selected time, then maybe you are printing your "proper proof" too dark. However, if it is "hard to tell" if more detail is there, then you're likely fairly close. You're obviously shooting 135, and are, rightly, checking the sprocket holes. Keep in mind, however, that there will always be a little outline of the sprocket hole even when the blacks of the hole and the film base are the same. If you're trying to get this outline to "disappear," then you're likely overexposing your contact print. If you need more than the sprocket holes to compare to, leave a strip of paper uncovered by the film on your contact and compare to that. Again, the outline of the edge will still show up when the blacks match. If you're happy with how the blacks match and your proofs are "too dark, lacking highlights," then increase development time till you get the range of tones you like.
The whole reason for a "proper proof" is to see at a glance if you've under- or overexposed/under- or over developed etc. The assumption is that printing at a time that gives you a good black will show this. That said, you need to spend some time living with and understanding "black" as relates to a fine print. Viewing light makes a big difference. Do a test strip without any film at all and well into the black range. You'll find that the blackest strip in dim light will have significant separation from its neighboring strips in brighter light. It's the way your eye works. If, like me, you plan to exhibit your prints and expect rather bright gallery lighting, then evaluate under those conditions. I often check my test strips in direct sunlight, but keeping in mind that the detail rendered under such bright light won't be visible under dimmer lighting. It's always a compromise to fit an "ideal" amount of illumination.
If you really want D-max black from clear areas of your negatives (and many of us do) then you'll likely find that you'll have to work at a significantly slower E.I. than box speed and, when those clear areas are printed max black, you'll sacrifice some of the shadow detail visible in the negative. This, for me, is not necessarily a bad thing. It means I can dodge shadows selectively to dig for a bit more detail. Large-format Zone System practitioners often shoot at half of box speed.
And, since you're this far with photo processing, lets "qualify" those pesky terms, "push" and "pull."

Developing longer gives you more overall contrast on your negative; it doesn't speed up your film appreciably. Developing less gives you less overall contrast. Zone System practitioners use this to tailor their negatives to the range of tones in the scene they are shooting (along with the paper they use). Got a flat scene? Give it more development and vice-versa. Sure, you can use extended development to get underexposed film to look better in a final print (sometimes necessary when you're shooting in really low light), but you'll always lose shadow detail. This latter is what I call "pushing," not increasing development time to get more overall (and the correct) contrast. Pulling has less of a reason for existing; often it's just a sloppier way to "overexpose and underdevelop" to get more shadow detail instead of doing the tests (like the proper proofing you're doing).
In honing in on an optimum personal exposure index and development scheme for "normal" scenes, we may have to increase or decrease E.I. and/or development time to get to the point where the proper proof gives a full range of tones and the desired amount of shadow detail and the black we want. Once you are there, then the proofs can be used to monitor our actual practice in the field.
An aside on using the Zone System with roll film: My advice is: Don't bother. I use it exclusively for sheet film, where the process is slow and I can develop the negatives individually. For roll film I advocate the following: Find your personal E.I. and developing time for "average" or "normal" scenes for you. Calibrate these so the print well on a middle contrast grade. For 135 film, I like to aim for grade 3, but grade 2 is fine as well (I think developing for grade 3 yields a bit less grain). Then, shoot away with one caveat: For scenes that are contrastier than "normal," you'll likely have to adjust exposure. If you're using your averaging or center-weighted in-camera meter, overexpose by a stop (or two if the contrast is really high). This seems counter-intuitive, but it prevents the loss of shadow detail. The resulting overly-contrasty negative you deal with when printing by using a lower contrast grade paper (that's why VC papers go down to grade 0). (If you are basing your exposure on a shadow value, as Zone System guys do, then you won't need to make an adjustment; it'll already be there. However, most of us don't meter that way when shooting 135.)
Hope all this helps,
Doremus