It's not as hard as it first looks. Here's how to do it easily (and impress your captain/fo at the same time

):
Everyone knows that certain numbers are easily divisible by 3 (3,6,9,12,15,18,21,24,27,30,etc.). If you have to lose 18,000', it's 60 miles; if you have to lose 21,000', it's 70 miles. But what if your altitude is in-between those numbers? Notice that there are always only two choices (in this case 19,000' and 20,000'). The lower of the two choices will be 63.333 (call it 63); the higher of the two will be 66.667 (call it 67). The lower number will always end in 3, the higher will always end in 7.
Try another example: 13,000'--it's closest to 12,000', so the distance will be 4
3 miles. 14,000'--it's closest to 15,000', so the distance will be 4
7 miles. This always works, and with a little practice you can look at a number and tell instantly what the correct distance is.
This method is especially useful for the precision necessary for approach descent planning, particularly the op's original question about being at 2000' and 5 miles out--where is the G/S? At 2000', that's closer to 2100' (which would be 7 miles) than 1800' (which would be 6 miles), so you need to start down 6.
7 miles out. If you indeed are at 2000' at 5 miles, you're WAY high! (You should be at 1500' at 5 miles). If you're still confused, just ask the guy sitting next to you.