Is now the time to get back into stocks?

I was speaking with a reporter at the Detroit News Wednesday about Dow 10,000 when he asked me whether now was a good time for people who had stayed out of the market during its run up from early March, when the Dow was at about 6,547, to put some money back into stocks. Is this a smart thing to do? How many people out there will view this milestone as a reason to buy? And what should these buyers buy?

Before getting into my thoughts on these questions, here's a story about why one person bought and later sold Apple Inc. (APPL). I was speaking to a guy last month who had read my March 5, 2008, post which said that if Apple -- which was then trading at $122 a share -- ever hit $100, it could be a buy.

This fellow remembered the post and when the stock hit $99 in February 2009, he bought shares. Unfortunately, it kept dropping -- hitting a low of $85 the next month -- before rebounding to $184, at which point he decided to take his profits, fearing that Steve Jobs might step down as CEO, crushing the stock. While Apple has since gone up further, he's happy with his profit.