Mac, I see you are not a fan of AI cartridges, but I really don't understand why. Furthermore, I don't really see where the issues will come up you are discussing. As long as the chamber is in spec, reaming it to AI should not present any problems. As long as the smith is competent in the reaming job, the chamber should come out very well. The fact its a rimmed cartridge only makes the prospect that much easier.
Also, all the brass I will load for the gun will be fireformed for the chamber, and neck sized only after that. I won't reload the brass more than 3-4x, and I don't see where case head separation will be a problem, and I'm not going to to push the envelope with loads. I am simply going to work up loads as any sane reloader would, and watch for pressure signs. Once I reach that level, I am going to stop. If my velocities are less than I expect, so be it. Will I trash the gun? No. I will use it anyway. However, I have a good feeling that I can realistically reach my goal in an 18" barrel, or at least close to it. This will give me very good performance out of a very compact package, and will be fun to shoot (while using less powder than a .308).
Another thing, lets look at PSI limits for both the cartridge and gun. We know that the .30-30 round is limited to around 38-40k CUP. This was mainly due to the fact that the Win 94 action would not handle much more than that. Now, look at the Handi rifle. It will handle CUP levels of 52-53k, and PSI levels around 60k. We know this to be true as the SAAMI standards for the .308 reaches these level. However, this level is rather unattainable as .30-30 brass is relatively weak, so the brass becomes the limiting factor. Can you achieve a 2600fps load under 45k in an 18" barrel in the AI? I think so. But, as I have said, it will be a learning experience. But, there is always the option of using .375 Winchester brass, which is considerably stronger. I have used this brass in 7-30 Waters loads, and it worked well. There is little reason to think it wouldn't work in the .30-30 AI. Does it make the process longer? Absolutely, but its a labor of love. Some people like to tinker, and I am definitely one of those folks!