What did he say? Specifically that it was not two reservations? Or that the system should recognise it as a continuing stay?
Both are actually incorrect.
I suspect that the point of confusion here is that I have a DVC stay booked. The first night is a one-bedroom at Hospitality House. The rest of the trip is a studio at Hospitality House. I certainly have two confirmation numbers, which no one is disputing. However, I have what's tantamount to a nine-night stay at the same resort. The IT stressed that the system should and usually does recognize that. He postulated that the issue might be that I originally had nine nights in the studio before breaking off the first night into a one-bedroom.
As for your last statement, that's entirely possible. Having worked in the hotel industry for a time in that kind of customer support situation, I've been in precisely the situation you describe wherein I had special booking privileges that weren't otherwise accessible. What you describe actually would have been a termination-worthy offense there, as making temporary, fake reservations was a huge no-no in a complex multiple hotel chain system. But it's logical that Disney would do this to maintain customer satisfaction.
Having said that, DVC Member Services didn't help me with this. I actually went straight through Disney, as that's what Siri dialed while I was driving that evening. This individual (not the IT) said that they could have helped, but I reached my destination too quickly and had to go. The following morning, the system unlocked the rest of my dates. So, it may not be a special privileges issues anyway. It may be a known, accepted solution to the practice when the problem arises.
I followed up with IT after the fact because I wanted Disney to know about my experience. I spoke with the IT for a few minutes, and the person explained (in a rambling way) about the process. The system is supposed to identify a customer's entire vacation plan, whether the person has one or six different hotel stays on the trip. Obviously, that's just a good programming practice, and you indicate that Disney has/had it for FastPasses.
Since the digital system for Magic Bands didn't come until later, they surely programmed the two systems at different times. From a user perspective, a split stay shouldn't matter since a vacation is a vacation. However, the system is apparently susceptible to hiccups, which is what's creating all of this confusion.
In fact, I had a problem simply recounting the matter to the IT. We went through the usual boilerplate about OS and browser. I use Firefox, and he cut me off right there. Apparently, MDE has so many glitches that IT needs users to default to Chrome before advancing through additional troubleshooting steps.
Nicky, I sincerely appreciate your help in particular earlier in the thread. It was informative. The situation seemed strange to me because I also have a split stay coming up in a few weeks and just had a split stay last week. It's our default traveling style, at least at WDW. I was able to book my ADRs without any issues in each instance. I just don't think Disney has their ducks in a row on this one.