I've found the work of Stefan Molyneux to be very insightful with regards to this (his other work has also been pretty influential for me).
You can find his books for free here. I haven't actually read his book on this specific topic ("Real-Time Relationships: The Logic of Love") since I was following his podcasting and forums pretty closely while he was working up to writing it.
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I'm not signed up for cryonics. Partly, this is because I'm poor. Partly, it's because I'm extremely risk-averse and I can imagine really really horrible outcomes of being frozen just as easily as I can imagine really really great outcomes - in the absence of people walking around who were frozen and awakened later, my imaginings are all the data I have.
I'm sorry for your loss and that of your girlfriend, and I wish her grandfather had not died. While I'm at it, I'll wish he'd been immortal. But there are two mistaken responses to the fact that human beings die: one is to tout death as a natural and possibly even positive part of the human condition, and one is to find excuses not to deal with it when it happens. Theism with an afterlife is the first thing; freezing the dead person is the second.
In all likelihood, if and when I stop being poor, my bet and the money behind it is going to be on medicine, and maybe uploads of living people if there are very promising projects going on by then.
By "extremely risk-averse" do you mean "working hard to maximise persistence odds" or "very scared of scary scenarios"?
You're right that death while signed up for cryonics is still a very bad thing, though. I don't think Eliezer would be fine with deaths if they were signed up, but sometimes he makes it seem that way.