Plan my timeline for signing up for retirement and senior health benefits

Help me plan when and how to sign up for retirement and senior health benefits. Country (and state if relevant): [LOCATION] My birth month and year: [MONTH/YEAR] Spouse or partner, if relevant: [their age and work status] Work status: [still working / planning to retire on DATE / retired] Current health coverage: [e.g. through my employer, spouse's employer, private plan, none] Retirement income sources: [e.g. public pension or Social Security, workplace pension, savings - no account numbers] What I'm unsure about: [e.g. when to start my pension, how health coverage works after I stop working, late-enrollment penalties] Give me: 1. A timeline from now to [AGE] showing the key dates and enrollment windows that typically apply in my country, each marked [CONFIRM WITH OFFICIAL SOURCE]. 2. The main decisions I'll face (e.g. when to start benefits, which health coverage options to choose, what happens to employer coverage) and the tradeoffs of each, explained simply. 3. Common and costly mistakes to avoid, such as missing an enrollment window or assuming coverage continues automatically. 4. A list of documents to gather. 5. Questions to ask the official agency, my employer's HR, and a licensed advisor. This is general information, not personalized financial or legal advice. Don't invent ages, penalties, or amounts - rules change, so mark all of them [CONFIRM] and direct me to official government sources and a free counseling service if one exists where I live.