I have been to Israel several times (for college, kibbutz, family) but my husband has been there less. We are thinking of retiring there. I agree, you need to be in Israel a while to get a sense of the everyday life before you contemplate making Aliyah. In fact, you can consider such an extended visit as step 1 in your move. It is a significant change, physically and mentally, especially as we age. Although it may be obvious, there's a different psyche there, different physical environment, different social life, etc. If you're like me, you want to know how to find out what it's like to find a plumber, to rent an apartment, how to buy a car, how to figure out you really want to live. An extended visit will help you answer these questions.
I'm also looking for guidance about making Aliyah during retirement and would appreciate any practical experience people can offer who have already made Aliyah in retirement from the U.S.