The Numbers Game

This is the shit that keeps me up at night:

I mail in my $5,000 Roth IRA check every year.  Will I live to age 59.5 to get the tax savings (or to even enjoy the money)?

Is it more beneficial to pay an extra $200/mo on the mortgage, thereby decreasing the tax benefit but also decreasing the life of the loan, or put that $200 in the pre-tax 403(b) plan which would decrease my tax obligation now but pay later, once again under that 59.5 age stipulation?

If I can afford $200, why not $300?

What is the correct ratio of cash earning .75% vs. funds invested in the market which can fluctuate rather wildly lately?

Would having $xx,xxx at .75% be foolish to be earning such a low rate?

What's the minimum amount to have saved for emegencies that's readily available?

How much cash is too much to carry on you at any time?

I have five $10 sequentially numbered bills that I've been holding on to because...?

I have calculated my next three years of mortgage payments with extra principal payments so each month the ending balance on my loan ends with 00.00.  Who does that?

Besides me, of course...