Prof - here's a sketch of what I know. Please redirect if I have not addressed what you want to know.
The fellow who claims to have designed the 2.7 as Thiel being "very demanding", had little to no input on it. He was interviewed for the project, but was not chosen.
Those directly involved included Kathy Gornik - as listener-evaluator and executive from the beginning and quite conversant in Jim's approach, values and methods. Likewise Dawn (now Cloyd) was part of the mix since she was 6 years old. Rob had been on hand and paying attention since the mid 80s. I re-hired Walter Kling, who had been part of the start-up but left for an architecture career, as part of my escape team. Walter was a manufacturing genius and had good, analytical ears, but did not intrude into Jim's space. Walter left when Jim died.
After I left in the mid 90s, Gary Dayton became Jim's assistant. Reports are that Gary had a good ear and that he co-evaluated sonic considerations with Jim, but he was not an engineer. Gary was part, along with those mentioned above, of the "Thiel team" that evaluated the outside work of new product development.
The 2.7 was developed as a joint venture between Team Thiel, creating the topology and cabinet particulars and evaluations, with the engineering performed by lead engineer Tim Gladwyn at Warkwyn Enterprises in Canada with complete design capability and the resources of the Canadian National Research Lab, among the very best in North America if not the world. The 2.7 was complete before the New Thiel owners brought in their own design team for the post-Jim products. The process I saw was that Warkwyn would develop a prototype built on Jim's research and prior components and topologies and coaching from Team Thiel. That prototype would be sent to Lexington for evaluation and be judged as some form of inadequate, and Warkwyn would go back to work. The expense was enormous and unaffordable. I was visiting when the final 2.7 prototype was delivered and was able to compare it with the 3.7 in Thiel's listening room. I would judge it a completed design, albeit more similar in components and price to the 3.7 than prior model 2 generations to their model 3 siblings. All previous 2s would have used a smaller diameter midrange to cross more efficaciously with the smaller 8" woofer. The 2.7 has a huge electrolytic cap bank to roll off the bottom of the midrange where the 8" woofer wants to cross in.
You know how the two models stack up from your extended comparison.
So I suppose you could say that there was a core team at Thiel who were quite versed in what a Thiel speaker had to measure and sound like, but no one who could actually perform the engineering to get it there.
Your final question gets to the nit of it. All the work was on Jim's shoulders. Jim did not have proteges studying under him. Although lip-service and disagreements surrounded that MO, in fact Jim was introverted, solitary and a solo inventing designer. Not only did he develop the products, he developed the research tools to develop them. And he was effectively the CEO, a very hands-on manager. Thiel Audio was an extension of Jim's interests, talents and considerable abilities.
Great effort was expended trying to identify someone to take on Jim's legacy. Kathy tried to bring in engineering talent. That failed precipitating the company sale. The New Thiel owners likewise pursued that path vigorously. I wasn't part of that search, but I trust that such a candidate was simply not available.