I cannot tell you how many retirement income calculators I have completed, and I am also tracking expenses via a spreadsheet. Possibly I'm a little obsessive/compulsive? But - it eases my mind, particularly because we retired fairly early (60ish).
I agree with educating yourself and reading all you can, and having a trusted financial advisor, but in the end, YOU are the one who has to make the decision, based on your income, lifestyle, and risk tolerance.
In my situation I will have a couple of small pensions kick in at 63-1/2 and at 65. I'm divorced and was a trailing spouse for years - didn't start working regularly full-time until about age 50 so the SS options are a little different, if I understood the explanation correctly (I went in person to a SS office in Ohio). I can get half of my ex's SS at 66 (not 62 if you are divorced) and then get my own at 70. Appeared to be a much better option for me as the difference is several hundred $/mo than if I took my own reduced SS at 62 - the other option. This only works if you did not remarry until after age 60 and were married at least 10 years. If I have this wrong, somebody please say something and I'll go in again to SS. Got over a year to get it right as I am still 60.
I am finding it very hard to take money OUT of anything - much harder for me than putting it in was. So far, I'm just using cash savings or non-IRA investments, but the day is coming when I will probably need or want to start using IRA money - then I'll have to decide whether or not to use ROTH or standard - another agonizing decision!
A friend of ours said something to me this weekend that hit home also. His parents are in their 80s and failing mentally and physically. He referred to the retirement 60s and the "go-go" years the 70s as the "slow-go" years, and 80s as the "no-go" years. I'm trying to keep this in mind, and not be so afraid to start spending it. Regardless of how we feel, we will not live forever. A good reminder that I will never be younger than I am now, and to go for the gusto (as long as I stay under that 4% withdrawal rate
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