Any of that retirement income in regular IRA/401K (you said some in Roth which implies some not)? if yes, then that money is taxable when you pull it out or roll it over. It is also subject to required min distributions which frequently bumps you into a higher tax bracket. When you start taking social security, that income also determines how much of your social security is taxable.
Best strategy is to pull money from any taxable retirement accounts first. Delay social security. Leave the Roths alone until later. You can adjust how much you take out of the regular IRAs based on your income level and tax rates. If you don't need that money, you can take advantage of the lower tax bracket to roll over money into a Roth. You pay taxes on the money taken out but then not on the Roth income.
I retired at 53. At the time, COBRA was more expensive than the affordable care act. Check all options. Your income will impact the cost of your insurance, both for affordable care act and then for medicare. If you go with COBRA, that will be another reason to spend down the non-roth retirement accounts first.
My mother is currently in assisted living at $12,000/mo. I'm not a believer in annuities due to the costs. I'll keep that money in my own account along with control of the money.
Good advice.