Greetings, Hight, and welcome. You wrote:

<<I took an early retirement package (at 55)from a corporation because it was obvious they were going to outsource my job. I've taken a similar position with a small company (15 employees) with growth potential, and they are offering a 401K program. I believe it would be wise to take it, but am wondering if it would be wiser to convert my existing regular IRA to a Roth and leave the 401K alone. Or would it be FOOLish to do both. Can I have a Roth IRA within my 401K?>>

I can't really determine what you're asking here. I assume, though, that when you left your prior job you had the 401k plan transferred to an IRA. Now you're thinking of moving the IRA to a Roth. If that's correct, then look at that issue carefully. It may not be a good move for you. Much depends on how you will pay the income taxes due on the conversion, how long the money will stay in the Roth, what your tax rate is today versus what it will be in retirement, and the size of plus your desires for your estate. For a discussion of these issues and the considerations you need to make, see post 1567 on this board at http://boards.fool.com/Message.asp?id=1040013000441002&sort=postdate. You must do a similar conversion analysis for yourself.

As to having a Roth IRA, you can't do that within a 401k plan. However, you can participate in your new job's 401k and contribute to a Roth at the same time. For more on IRAs and 401k plans, see my Foolish Retirement Plan Primer at http://www.fool.com/Retirement/Retirement.htm.

<<Im a way, I'm starting over. Financial and health problems have reduced my savings to less than $20,000; however, I have eliminated almost all my debt. I should have it paid off this year. Between my monthly retirement checks and my new salary, I'm making close to what I was making at retirement (44G). Real retirement, I'm hoping by at least by age 70. So now what? Stock? Haven't had much luck. Mutual funds? Maybe. Long term CD? What would be the best strategy?>>

"Best" is in the eyes of the beholder. In Fooldom, we believe that decision is one that must be made by each person individually. You must invest in the way that makes you most comfortable. It's your money, and you're the one who has to sleep comfortably at night. We think that if you have five or more years before you need to see that money again, then stocks are the best route to go based on history. However, the ups and particularly the downs of the stock market cause some folks to panic in the short-term. Can you ride out the downs without having a great deal of upset? Only you can answer that.

Regards..Pixy