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In Robert A. Heinlein's The Door into Summer, Dan Davis, the hero, ends up cold sleeping twice (at the same time) and at different facilities, with different insurance companies.

When he wakes the first time, before the time loop back, he learns that Mannix squandered all his investments. Did that actually happen?

In other words, when Davis went back the second time, was he able to convey his assets to the other (legit) insurance company? Or did he just "buy a ticket" the second time?

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Only Mannix/Master gets the assets. By the time the second go-round occurs, Dan no longer is worried about his 1970 Hired Girl (or any other) assets.

Dan started with Mutual Insurance, signing the papers, but failing the medical exam. When he's captured and drugged by Belle and Miles, Belle changes the paperwork to say "Master" (because it's close to "Mutual" and she used to work at there):

“Yes, ‘Master Insurance Company of California’ .. . and there’s room enough on each of them. I wish it could be ‘Motors’ instead of ‘Master’; that would be a cinch—but I don’t have any connections at ‘Motors Insurance,’ and besides, I’m not sure they even handle hibernation; I think they’ re just autos and trucks.”

Master was bought out by Mannix and went bust while Dan was asleep.

The next time around he didn't have an estate to invest, but he used cash on hand to buy the minimum service from Mutual:

Powell was much annoyed that I had canceled my arrangements for Mutual to handle my estate and was especially inclined to lecture me over having lost my papers. “I can’t very well ask the same judge to pass on your committal twice in the same twenty-four hours. It’s most irregular.”

He smoothed that (and other issues) over by threatening to go elsewhere:

But I don’t care whether it says ‘Mutual’ at the top or ‘Central Valley.’ Mr. Powell, I’m buying and you’re selling. If you don’t sell what I want to buy I’ll go where they do sell it.”

Dan doesn't want to change the past, he wants to fulfill what he knows resulted from his unknown actions (there's another Daniel who owns a company making advanced products that are designed just like he would have designed them and that Daniel is married to Ricky), so he doesn't try to prevent Mannix from wasting his first fortune (from his first primitive designs) - after all, he knows there's a second, bigger one waiting for him.

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    Perfect. No longer had a copy to check myself.
    – Anonymous
    Commented Jul 17 at 11:19

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