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1. What do the "wise ones" suggest as a mix between CD's, bonds, stocks, mutual funds for someone who wants to see their money grow but couldn't bear to have everything he owned riding on the stock market.

My calculations are you have 40% in CDs and 60% in stocks. The stocks are in mutual funds and individual issues. 40% Fixed / 60% Stocks is what the "wise ones" would consider a conservative investment mix. Most that I've talked to consider any more in Fixed to be too conservative.

4. I have about 60k in one bank stock handed down to me from my grandfather. I don't have any idea of what the capital gains tax would be if I sold it (since the stock was a startup of the bank) but I am sure the tax would be significant. How do I analyze whether or not I should sell them and put them into my Index Fund? This is a small hometown bank and my gut feeling is that it will get gobbled up one of these days by a megabank and the stock may be worth more at that time than it is now.

If he gave you the shares while alive, your cost basis is his cost basis. If you inherited them, your cost basis is the market value on his date of death.
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