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O’Leary went 52-33 at GT and 81-68 at UCF with five years of nine wins or more.

As you said, the issue is guys who get good jobs did well at small jobs. Guys who get very god jobs often did well at decent to good jobs (Rich Rod).

so the best bet is coordinators who jumped in (Weis) or guys with short first stints.

Darrell Hazel is a good one
Chris Ash
Stan Parrish 9-51-1 in six-plus years at K State, Ball State and three interim games at EMU.

Will Muschamp is an interesting one because he’s had two good seasons and another that was close to as good as you could expect in eight, with two bad and three blah. Florida should be better than it was, South Carolina, maybe a little. McElwain was modestly successful On average, though his personality let to a quick ouster when it went bad.

Edit: My fun fact was wrong because the spreadsheet was limited. I regret the error.

OU's three winningest (in order of # of wins) HFCs--Bob Stoops, Barry Switzer, and Bud Wilkinson--were all major-college coordinators (Bud and Barry at OU)--not small-college HCs--before taking over the Sooner program.
Back to the topic, OU's worst HC was John Blake.  12-22 from 1996 through 1998.  Worst three-year stretch in program history.  Lowest winning % (35%) of anyone except a guy who went 0-1 in 1895.

I think Les Miles deserves an honorable mention in this category. He did less with more than virtually any other coach. I really miss him. 

During the RichRod/Hoke years, Wolverine fans would have crawled across broken glass from Ann Arbor to Baton Rouge in order to have Les Miles as their HC. 

Or?

I think that was when the Wolverines and Harbaugh were feuding over his status as a Michigan Man. 

What are the most famous 'bad' coaches ever?  Along the lines of Lane Kiffin, from the perspective of a Tennessee fan. 

The more commonly known, the better.

It's a REALLY hard question... Most terrible coaches don't ever have enough notoriety to be counted. Kiffin wasn't even a terrible coach, from the perspective of a Tennessee fan. He's hated because he left--and how he left--not because he was a terrible coach. 

I'd nominate Darrell Hazell, of course.

• Was never a head coach prior to his Kent State job. Assistant under Tressel at OSU.
• At Kent State (historically bad team), he had one middling year and then one really amazing year.
• He got the Purdue job, didn't bring his coordinators from Kent State, and proceeded to be the historically worst Purdue coach in our history. That's not hyperbole--he was TERRIBLE.
• He did so in several ways. Poor recruiting. Poor hiring (John Shoop?!?! as your OC). Poor player development. Allowing Shoop to create an overly-complex offense that the team couldn't execute because the playbook was too big for college players. Shoehorning a pro-style offensive scheme into a school where the talent wouldn't support it.  

After Purdue, he [rightly] got kicked down several notches, going from college head coach to position coach (WR) in the NFL. After just two years of that, and at only 54 years of age, he retired from coaching. 

As a man, I respect Darrell Hazell. He seems like a really stand-up guy. As a coach, he not only failed the Purdue program as a coach but left a smoking crater that Jeff Brohm has spent the last 3 years trying to dig out of. Hazell was so bad that with a <.500 record, Jeff Brohm is already looking like a miracle worker just to make the team mediocre. 

OU's three winningest (in order of # of wins) HFCs--Bob Stoops, Barry Switzer, and Bud Wilkinson--were all major-college coordinators (Bud and Barry at OU)--not small-college HCs--before taking over the Sooner program.
Back to the topic, OU's worst HC was John Blake.  12-22 from 1996 through 1998.  Worst three-year stretch in program history.  Lowest winning % (35%) of anyone except a guy who went 0-1 in 1895.

This isn't to say that hiring a coordinator is bad, but when you're looking at really bad head coaches, coordinators who get big jobs tend and are bad don't have the backing of having been good HCs at any point. Now some were not very good HCs  before they got the good jobs (Hazel, in some senses Hoke), but it tends to cut into the bad HC resume. 

(One early job story I think is fascinating is Urban Meyer's BG tenure, as it was kinda less glorious than it gets treated now)