What a total mess it is to retire! I am only 56, so I have a few years to plan, but holy moley, what a mess everything is.

• If you don't apply to Medicare during a certain timeframe you get permanently higher rates, unless of course if you have an HSA (and I still don't understand what the difference is).  There are also several plans that you get locked into once you choose them
• Starting SS at different ages changes how much you get. Again, permanent, but you can back out within one year if you pay it all back. Many predatory companies twist this information to entice you to pay their fees to get basic information (free chicken dinners to hear their spiel).
• Paying tithing via any method other than through a QCD results in higher taxes, but only after age 70.5, and if you don't follow a very specific method to report it to the IRS, they ignore it
• There are strategies of paying tithing every other year to reduce taxes
• You can pay tithing/charity into a special tax-free account and only disperse it to a beneficiary at certain times (including missions, interestingly enough)
• 401 K (Tax Deferred), ROTH (Tax Free), Normal IRA's, etc. All different, all affects taxes differently, all have different "gotcha's" that can affect your taxes. When you pull money from these (or are forced to pull money) over the years affects your taxes.

What a complete mess! There are also companies that would LOVE to charge you a lot of money to help you "set it all up".

I am absolutely NOT a bit-twiddler when it comes to investments and money. My brother just retired two years early (he is 65) and I don't think he realizes how much that will affect his SS over the years.

The sad thing is that over the next 11 years it will probably all change anyway and everything I have learned will be useless.