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Nixon got the nomination in 60 as the incumbant VP under Ike, and as you said lost narrowly to Kennedy. In 68, when he ran against Humphrey, he was an established GOP “leader” which helped him get the nod for the nomination.

Reagan ran a good primary campaign in 76, but lost the nomination to Ford, the incumbant president. That was a very tightly fought primary, and even though Reagan didn’t speak ill of Ford he also declined to campaign very enthusiastically for him. Ford blamed Reagan in part for his loss to Carter in the general election in 76. Reagan’s organization was still very much intact after the general election and Reagan kept building his coalition in order to be positioned for the 1980 primary as the dominant GOP leader. Bush ran a decent enough campaign for Reagan to decide he would make a good running-mate. (Reagan passed over Dole - who had been Ford’s running-mate - and over Kemp - who would have been a more conservative choice than GHW Bush.)

GHW Bush was pretty much a given in 1988, the incumbant VP for a very successful 2-term President who had turned the country around from the dismal Carter years to a path of long-term economic growth with low interest rates and low inflation.

After Bush lost his reelection bid in 1992, that left the field wide open in 1996. As Dole had been bidin’ his time in the Senate after his unsuccessful VP run in 76 and his unsuccessful attempts at the nomination in 1980 and 1988, he ran on pretty much an “it’s my turn” platform for the 1996 nomination, along with a side order of “who else do you think is electable?” and the GOP primary voters decided that nobody else was groomed enough for the nomination. I personally think either Kemp or Gramm could have run a stronger campaign than Dole, but we got what we got, and clinton won a second term rather easily.

In 2000, there weren’t very many viable GOP candidates positioned for the nomination. Fortunately, GW Bush got out there and got a lead ahead of McCain, or we might have had McCain to run a dismal campaign against algore, which probably would have made algore the Commander-in-Chief on 9/11/2001. THANK GOD we avoided that disaster.

In 2008, with nobody positioned to take up the conservative mantle, we had a free-for-all in which Huckabee, Romney, and McCain splitting up the Anybody-but-Guiliani majority, which almost enabled Guiliani to mount an early lead. (Fortunately, he turned out to be an awful campaigner.) Fred Thompson probably waited a little too late to jump into the campaign, and the groundswell of support that he was building melted out from under him before he got his campaign underway. As the herd started getting thinned, and it got to a point that Romney had become the most palatable of the RINO’s left, McCain emerged with what was essentially an “it’s his turn” nomination.

So, I’m not sure that the GOP side really has a tendency to nominate those who have had multiple attempts at the nomination, but it definitely appears that the 1996 and 2008 nominations were of the “it’s his turn” variety. We definitely need to take a better approach in 2012. (And I ABSOLUTELY believe that a Huckabee or Romney nomination would NOT be the winning approach.)

there are some parallels between the Reagan campaign and Romney (before anyone flips out i am comparing the campaigns not the people nor their conservative bonafides).
Romney ran a pretty strong second last time around as Reagan did in 76. Not as strong as Reagan mind you but a good run.
Romeny is keeping his team intact. they meet quarterly if not monthly and he keeps his PACs going as well. the infrastructure is still there.
He campaigns for GOPers.
He has deep pockets and connections to other deep pockets.
Do i hope he will be the nominee? heck no i am just saying that he is well positioned for another run and has a decent shot at the nomination. especially if there are a ton of people vying for the nomination kind of like how McCain pulled it off this time around