Should I convert my traditional IRA account to a Roth? I am 86 years old and I am in the highest tax bracket.

The three main issues to decide when considering a conversion are:

  1. When will the money be needed? (at least a 10-15-year time horizon)
  2. What will future tax rates be? (compared to current tax rates)
  3. Where will the money to pay the tax come from? Ideally, it’s best to pay the conversion tax from non-IRA funds.

You might also consider a partial conversion over a period of years. Generally, seniors who don’t need the money probably should consider a conversion. Because of your age, you are not doing the conversion for yourself; you are doing it for your Roth IRA beneficiaries. Please note that your required minimum distribution cannot be converted and must be taken before you convert. You should speak with a financial advisor to discuss your situation.
Will I be required to begin taking out Required Minimum Distributions out of my three Roth IRAs when I turn 70 ½?  They are not inherited Roth IRAs, and I own no traditional IRAs or 401Ks.

Good news - you never have to take any required minimum distributions from your Roth IRAs at age 70 ½ or anytime.

I have a rollover check over 60-days old that I'd like to deposit into a qualified account.  Can I do that and not be subject to the age 59 ½  penalty?

In an IRA-to-IRA rollover, the 60-day rollover period is measured from the day you receive the check. If it’s past 60 days from when your received it, the funds are not rollover eligible and thus are taxable to you. Also, because you’re younger than age 59 ½, the 10% early distribution penalty will apply unless there is an exception to the penalty, such as disability.