It reminds me of the old story of a king who was looking for a new driver for his carriage. He took the three best candidates out an asked each of them the same question: "How close could you drive me to the edge of this cliff?" The first responded, "Your majesty, I could get within a foot of that cliff." Not to be outdone, the second answered, "I could get you within 6 inches of the edge." When the question was posed to the final candidate, he looked at the king and said, "Your majesty, your life is far to valuable. I would not go anywhere near the edge of the cliff." Guess who got the job?
Personally, VFR or IFR, I try to never exceed 3.5 hrs en route, and generally try for under 3. With 5 hours of fuel, that allows for the possibility that I didn't get as many gallons in as I thought, headwinds are stronger than I planned, or any other number of variables. If I'm going to Oshkosh, my planned stops are usually legs of 255NM, 172NM, 174NM, and then whatever it ends up being from Dodge County to KOSH with the full arrival. The longest leg of that usually ends up being about 2.5 hours or less. On our trip to the Bahamas, I stretched it to 3.5 HOBBS hours on 3 separate legs, but with a pregnant wife in a 172, options are limited.