When I recable an Oldham/Zoom box setup, these days I use regular rubber mains cable (can't quite remember the diameter at the moment).
At the headset end, I solder 3.2mm bare ring terminals to the cable and cover the terminal shafts with heatshrink (which might need threading on beforehand if it won't fit over the ring terminal)
For the cable fixing, I leave the headset cable entry bare (no brass cable attaching ring), poke the cable some way into the headset and tie a standard 3.5mm cable tie around the cable outer very close to the end.
I then mix up some quick-set epoxy, and plaster some around the cable behind the cable tie, and some on the headset shell around the cable hole, then pull the cable into position and leave to set. Depending on epoxy fluidity, it might be worth leaving doing this for a minute or two until the epoxy is less likely to run everywhere.
Afterwards. more epoxy or silicone could be added on the outside, depending on what kind of gap is left between cable and surrounding headset.
Personally, for a neat finish I use a sleeved cable grommet which is undersized (and has to be stretched to fit on the cable) with the headset end trimmed to fit inside the headset hole. It's a bit of a faff to get on on the right position, and probably not really worth someone buying a pack for a one-off job, but it does look good (a 'cosmetic strain relief'), and helps stop fluid epoxy running down the cable before it sets.
To get the overall length right, I fit the box and headset to the helmet, feed the cable into the box base, pull the cable tight from the headset to the left 'leg' of the battery box, and leave a small curve of cable below the box (ie, I don't pull it ultra-tight). Eventually I'll pull the cable taut from the headset and cable-tie it to the left leg, so a little slack below the box isn't an issue, and can come in handy in case of cock-ups or moving to a different helmet.
I mark the cable just below the box with a magic marker (hard to see afterwards, but usually visible even if only by shininess) and then remove the headset from its bracket and pull some cable through into the box until I can see the mark. A cable tie a few mm above the mark is fitted and trimmed, and I can refit the headset on its bracket and pull the cable back to see if the tie is in the right position on the cable. If it is, then I can use the cable tie to get the lengths right for cutting and connector fitting.
If I'm using regular mains cable, I'd cut it so that when the cable is pulled tight with the cable tie at the box base, the whole Tamiya connector can be pulled clear of the box by 5-10mm to operate the catch easily - holding the connector in position next to the cable gives a reasonable idea of where to cut it.
After cutting, I strip the outer sheath from a few mm above where the cable tie is, then strip the ends, attach the connector contacts, silicone grease the pins and cable ends and fit the pins into the connector [the correct way round - at least for the standard Tamiyas, Red-Square is how I remember it].
If at this point I try things out and find I'd made things a little short, I could always use some of the slack I made earlier, removing the cable tie and fitting another one a little further down the cable.
Once that's done I can do the final tightening and cable-tying of the cable to the battery box leg to keep it snug and avoid snagging, and that's it.
One point is that there isn't a huge amount of spare height with either kind of Tamiya connector, so the closer to the cable tie the sheath is trimmed, the more space is available for things to fit above the end of the sheath. Leaving a cm or more of sheath could make things awkward.
I like to use releasable cable ties for the box lid - if they're looked after and not unnecessarily tightened they are pretty durable and easy to open.
When it comes to stripping outer sheaths, I tend to do it by carefully and slowly working round the cable with a small penknife blade, bending the cable to see things more clearly, and being very careful not to nick the internal wire's sheaths.
With proper Oldham cables, the spiralling wires inside are longer then the overall cable is, meaning that, for example, stripping 35mm of sheath would give about 60mm of wire.
If there's anything I haven't made clear, do ask for clarification.