What if we assume Period Independence except for exact repetitions, where the value of extra repetitions eventually go to zero? Perhaps this could be a way to be "timid" while making the downsides of "timidity" seem not so bad or even reasonable? For example in section 6.3.2, such a person would only choose deal 1 over deal 2 if the years of happy lives offered in deal 1 are such that he would already have repeated all possible happy time periods so many times that he values more repetitions very little.

I think it would be interesting if you could show that the space of possible periods-of-lives is structured in such a way that, when combined with a reasonable rule for discounting repetitions, yields a bounded utility function. I don't have fully developed views on the repetition issue and can imagine that the view has some weird consequences, but if you could do this I would count it as a significant mark in favor of the perspective.

BTW what do you think about my suggestion to do a sequence of blog posts based on your thesis?

I think this would have some value but isn't at the top of my list right now.

Also as an unrelated comment, the font in your thesis seems to be such that it's pretty uncomfortable to read in Adobe Acrobat, unless I zoom in to make the text much larger than I usually have to. Not sure if it's something you can easily fix. If not, I can try to help if you email me the source of the PDF.

I think I'll keep with the current format for citation consistency for now. But I have added a larger font version here.