It doesn't really matter which software you use... you shouldn't be worried about whether your heatsink/fan is adequate because if you bought an OEM CPU, you should have bought an approved heatsink/fan. If your CPU is retail, you shouldn't be overclocking cause that will void your warranty, and the heatsink/fan that comes with it isn't meant to cool an overclocked CPU.
The process for checking your temps is fairly simple... as soon as you install everything and turn the computer on, immediately enter the BIOS and go to the hardware monitoring section and keep an eye on the CPU temp. If it jumps up to 60 degree C or higher, something's wrong, shut it off and make sure the heatsink is mounted properly. If it stays reasonable, then go ahead and boot Windows... run a few CPU intensive programs to get the temps up and check to make sure temps are reasonable. Now you have a baseline. Overclock to whatever you want, check stability and temps along the way to make sure things aren't getting out of hand.
The reason one spec doesn't apply to everyone is because all motherboards are different... they take temperature readings from different areas of the motherboard. General rule of thumb, if you touch the base of your heatsink with the computer on, and it's hot enough so it's uncomfortable to leave your finger on it, it's too warm and you should look into better cooling, or reduce your overclock.