If you're in the opposition research business - and there are plenty of people in that business - your life-long fantasy is to get your hands on an opponent like Trump.
I think Trump is generally a decent guy who is right about a LOT of economic issues, but he would be a DISASTROUS political candidate, at any level. At the national level, it would be Hindenburg bad.
My concern with him is that he's yet another celebrity (like Schwarzenegger) who talks tough but once he gets there, you find out it's all show. (Remember Arnold's talk about disbanding the unions in Sacramento? And how'd that work out?)
I get what you are saying, however isn't it possible for that to be so obvious that the effect, rather than being magnified, is actually reduced? Come on ...it is The Donald we are talking about. Who doesn't know about his divorces, penchant for beautiful women, spending habits, etc. If, to use an example, I said that Billy Graham loves to spend money on fast sports cars, people would raise an eyebrow. If I said, however, that Kobe Bryant likes to spend money on fast sports cars, the question would be 'how fast?' Donald would not be running on the same platform as some of the other candidates who need to claim how they did not inhale or they tried wicca but are not the devil's handmaided. Trump is known as an aggressive, risk-it-all, business person who has forged a name for himself for being hard-nosed and fast-talking, and living the big life. Basically the business world's version of Don King to put it bluntly, but just like Don King in boxing promotion, having the track record to back up the overtness. I can see a lot that opposition research may want to target (e.g. the love of women, the fact that he has been bankrupt twice and almost a third time, the fact that he is uber aggressive, etc), but I do not see anything that they can actually use. There is nothing sticky, nothing that people do not already know, and even if it came out he did drugs in the 80s (and with the culture then I would not be surprised) or 'hired' female services (or any similar demerit), most of the populace would more or less expect it of him and give him a pass. Actually some of those 'problems' would actually be key advantages ...for instance his bankruptcies would show that he knows how to make it back from the brink (obviously it is more complex than that, but in the world of soundbytes that would be sufficient).
In my opinion, and I could be wrong, Donald Trump is almost walking teflon. Sure, there is a lot of material out there on The Donald (and I am sure a lot that is not public knowledge and would be quite damning for most people), but for something to stick on Trump he would have to be photographed eating the entrails of a nun sprinkled with pre-teen livers. On a serious note, he would be a very hard target. Not because there is not a lot of material on him, but because of making it stick. His brand, unlike many politicians who (act) like they are lily-white and 'have never told a lie,' Trump doesn't have that. His brand is based on results, and when there is failure the appearance of coming from failure into even bigger results (and that is quite a strong appearance for Trump). In a time when the economy is still the number one issue, a tough businessman who seems to know what he is talking about can easily be elected to be CEO of a country.
And to be honest, I totally believe that Trump could do a better job than Obama+WBush+Clinton+PapaBush combined. Certain of that.
Furthermore, unlike most politicians, he is an absolute pragmatist. What he is saying about diplomacy and diplomats is true, and while there is a time for diplomacy it is not when one is against the ropes. The US is still the strongest most innovative nation in the world, but it has been ceeding some of that lead (unnecessarily) to China in particular. Since Deng Xiaoping rise in China in 1978/79, that country has moved from a place that was known for rice, bicycles all over, and really bad KungFu films to the second largest economy in the world. Add to that a weak domestic economy, and I doubt most voters would worry much about Trump's many experiences with women as compared to his ability to do something about the economy. He is obviously no social conservative, but I would bet good money at fair odds that come 2012 many many many people will be concerned about someone with good and effective business sense that can actually do something about the economy (not Obama's pixie dust hope and dreams, and not G.W.Bush needing to 'kill capitalism to save it'), rather than someone with the appropriate social conservative credentials. Sadly, bad economic policy by both parties has led to the need for a business minded leader rather than someone who 'says the right things' but knows next to nothing about how the economy works.
Maybe America does need a CEO.