Leeds United were the biggest gamblers of all.
Manchester United went for a methodical, slow and steady approach with a very organised, determined manager who they trusted and was given sufficient time and funds to realise his potential.
I think I know which model I prefer - I have always believed the opposite of what the poster is alluding to - that patience in a manager and system is a virtue in club development, that one season too many is less harmful than one season too few. I think the evidence of the great dynasties in English football supports that supposition. The resources wasted on changing tack before you know for sure the system's broke are simply wasted resources, not brave bets.
Ah, but your talking about two different types of risk, short term and long term;
A: Leeds risked all on a short term 'safe bet', which was to invest heavily to build a squad to challenge for the title and get into the CL. This short term, but very risky, bet did not pay off at all and the club almost folded.
B: ManU risked a considerable about of time, in giving Ferguson 5/6 years to win the league, after all if he had failed, Utd would have had to try and build again, probably by giving the manager 4/5 years.
So both of the above scenarios were risky (to a varying degree) and no-one played it safe, imagine a slightly different world that Ferguson had lost the FA Cup replay and been sacked. Suddenly its the mid-90's and Liverpool/Blackburn/Arsenal dominate and become the comercial colosus that utd did.
The 'risk' that the OP is talking about, in my oppinion, would be something like;
A: Give Rodgers 5/6 years even without CL football to build a dynasty
B: Decided to go down the route Bilbao did and say, we'll rely on our academy and only have scousers/north-westerners playing for us, with maybe 1 'foreign' player
I don't necessarily agree with the OP, but I don't think he's talking about Leeds type risk