I have had a pensioner LTR since January, 2023. If your finances are simple then applying yourself online is very easy. As far as travel goes, you don’t need re-entry permits and you can use the fast track lane at the airport but no one will meet you and drive you around. One year reporting, not 90 day reporting but if you are traveling often you would never report. Obviously much much less expensive. If you are over 50 I don’t see how the Thai Elite makes much sense. For the few interactions you will have with them, you will find the staff at the Thailand BOI to be friendly and a pleasure to deal with.
I bought a new car in Bangkok in 2022. The only deposit was 10,000 baht to secure my name on the list of customers waiting for a car to become available. At that time I waited 4 months. Once the car arrived I just transferred the full price using my banking app. I was on an OA visa and I needed a residency certificate and my passport. I think that was all there was to it. A year later I moved to Sisaket province.
As long as you are here on the proper visa then I wouldn’t think you should have any problem switching from one visa to another. Sometimes people staying in Thailand on educational visas as students have future problems but it sounds like you are pursuing a work visa at a university.
If he is in the very first year of the OA visa then he cannot cancel it. He has to wait until that first year runs out. The original visa has to expire. After that you have options.
Unless it is one of a kind or has sentimental value I wouldn’t ship anything. Anything for day-to-day living you should replace in Thailand. Six years after moving here I shipped some artwork made by my father who died 20 years ago. The shipping was expensive but it has sentimental value.