Thank you all for the great suggestions and help! It's so awesome to see that everybody is so friendly! :)

In general I feel that it might be a great adventure with the possibility to succeed. I feel we are perfectly fine to turn back any time, we would consider it as a preparation for a second attempt.

nyker: thanks for your advice! no we don't have any high altitude experience. That's the main reason I'm so unsure about our success. Both of your suggestions are awesome, but unfortunately I'm based in San Francisco and both of those peaks are quite far from me. Although instead of Mt. Whitney we will consider those this June. I will read about those peaks and then decide what to do.

Chicagocwright: that's really promising, thank you for sharing. I will try to expose myself to higher altitude and see if I need diamox. But it's really good to know that you had positive experience with it.

Steve C: wow! Mt. Dana seems such a perfect warm up hike! I have no idea how I missed during searching for hikes before Mount Whitney. I think I will definitely take your advice and see how sensitive I am to AMS.