What to Choose?

Why is Health Insurance, 401k's and money all so confusing?
I mean I think I am a fairly intelligent woman, with a Bachelors Degree in Engineering, I should be able to figure this stuff out, right? Wrong I am just as confused as everyone else in the world. Many of you may or may not know that I am a little, OK maybe a lot, OCD about money. I hate making big decisions that could potentially turn out badly. Since it is the end of the year I have to make all these decisions about:

what health insurance policy to be on?
if I am going to put more into my 401k?
do I want Short Term disability?
do I want to go on a Aflac supplemental insurance (Short Term, Cancer, ICU, Hospital Stay, ect..)?
do I want vision insurance?
do I want a HSA (Health Savings Account)?

I hate making decisions it literally eats me up inside. If money grew on trees I would max out my 401k, sign up for every insurance possible just to be sure I am covered. But it does not, so I am stuck here wondering what to do.

Here is what goes through my nerdy head:
Will Short Term Disability Pay off or would I be better just putting the premium in savings? Would it be smarter to just have a health saving account to pay for glasses or does vision insurance make more sense?
Should I increase my contributions to my 401K by 1%, 5%, more, or leave it where it is?
Am I going to be able to retire some day, or will I have to work forever!!!

That said Mike and I are truly blessed to have great jobs and have all these options available to us. I thank God everyday that we have health insurance, good jobs, a roof over our heads, and each other to complain to.

But why can't God just come out and tell me what to do.