OK, many interesting responses - thank you.
First of all, the containers I use are these stainless steel primary fermenters:
https://www.amazon.com/gp/product/B018J82JOY/
They are 14 gallons in size. There are not 11 or 12 or 13 or 13.5 gallon sizes so no matter what I am going to have 1 or 2 or 3 gallons of headspace. Note: they are perfectly airtight - gasketed with 5 clamp locks and I have tested several of them with fine vacuum gauges over months and they lose no vacuum. So they are tight.
This is a single vintage, single vineyard product I am making and my 400 grapevines make what they make - if it comes out to 11 gallons that is what it comes out to.
Yes, certainly I could get a 7 gallon fermenter like this, and a 5 gal carboy, and then ... mix and match containers like that but not only does this diminish any real value in bulk aging prior to bottling it also adds more reps and more variables AND dosing and measuring additives like KMBS or acid are double the work and different calculations, etc.
So the bottom line is, the 11-13 gallons that my vineyard makes is going into one final container - this one.
Yes, this is where I am going as well ... although you're saying start with 100% ambient air and cut it by halves with each rep - I would be more aggressive and dump co2 into the headspace initially, like I have been, AND THEN cycle the vacuum/co2 for a few reps.
So instead of 50 -> 25 -> 12.5% ambient air, I would be going 5% -> 2.5% -> 1.25% ... (assuming I had only 5% ambient air initially).
... which means a second hole drilled and cleaned up (and gasketed) on the lid. That's pretty easy and I can vacuum test it with water and air for a month and be sure it doesn't leak.
Here are some closing thoughts:
1) I would, still, really like to hear from some lab tech somewhere - or some industry tech - not connected to winemaking. How do people do this in a lab ? I don't think they're using plastic baggies. They MIGHT be using a co2 generator like dry ice but, again, I'd love to hear something that sounds like "the real way people do this".
2) It seems to me that there is a difficult valley between very small production (2-5 or even 9-10 gallons) and, say 500 or 1000 gallons. Everyone knows exactly and perfectly how to deal with one or two carboys. At the same time, I think the pros at big wineries have very nice (and very expensive) methods of dealing with 500 or 1000 gallons. But if you have 15-30 gallons you're stuck (re)inventing things.
Does that ring true to you ?