I just keep tightening it a lot and then try to wiggle the heatsink. If it wobbles at all, then you definitely need more. If it doesn't, and it's like it pretty much part of the motherboard, then you're probably good.
With my Tuniq Tower, it's really tight against the motherboard, but I can still turn the screws a little more. I haven't gotten to the point where it wouldn't turn at all, but that would probably break the motherboard. But still, it's pretty hard to turn the screws.
Once you start doing it, I'm sure you'll be able to tell if it's good enough or not.
And if later you decide that it isn't tight enough, you can always tighten it a little more. I usually twist the screws a little when I dust out my case, just in case it comes a little loose over time.