Would never be so presumtous as to agree with your comments AMEX ;o)
I concur with niknak, go and get some commercial experience with another operator first. If you do want to just jump in at the deep end (and it has been done, but rarely successfully), then you will need some good financial backers behind you - people who will not want to see a vast return on their money and who, preferably, will not want to see their investment back!
In the old adage "to make a million in Aviation, start with ten".
Bear in mind that the entry level is no longer Navajos and Senecas - they serve a very small niche market which is rapidly disappearing. King Airs, well, see the other post that's kicking around here about them and you'll see that we're all in rough agreement that turboprops aren't really a great business decision either these days.
I hate it when the customers get picky! Everyone wants jets...
Would like to say I hope that the above doesn't put you off, but I guess it's not really that positive! If you fancy a challenge though, give it a shot, but be careful how much money you chuck at it (and start by talking to other operators about piggy-backing off their AOC's. It'll give you the opportunity to gauge whether or not your plan would work).
ATB, Daifly.