There are many ways to generate an estimation of error. First, a plug.
If you have an interest in experimental physics, or are an aspiring theoretician who wants to understand the voodoo that goes on in a laboratory, you should pick up a copy of "An Introduction to Error Analysis" by Taylor. It's one of the friendliest, well written, most brief, easily accessible books I've ever seen. It's written in the style of Div Grad Curl, or a David Griffiths textbook.
Let's agree on some terminology. When you report a measurement, you should always report it as:
[tex]
x = x_{\hbox{\small best}} \pm \Delta x[/tex]
where [itex]x_{\hbox{\small best}}[/itex] is your best estimate for the value of x (it would almost always be the mean of your measurements), and [itex]\Delta x[/itex] gives an estimate of the error in your best guess. There are many, many ways of calculating error. However, for repeated independent trials, you should be using the standard deviation of the mean (SDOM) for [itex]\Delta x[/itex].
What you'll find is that by using SDOM, the more measurements you make, the smaller the SDOM will be. If it doesn't get smaller, you're most likely doing something very wrong.
You should be aware that there are two very different things here:
1. generating an uncertainty for a single quantity due to repeated measurements.
For example, you take 10 length measurements of the length of a table. That's what you're doing. One good way of generating an error estimate would be the SDOM.
2. generating an uncertainty for a function of several measurements.
For example, the table is much longer than your ruler, and so you need to take 3 sets of measurements. Each set consists of 10 "trials". Hmmm... lame example, but you get the idea. A better example would be measure the length, width, height of a box to calculate a volume. The rule you stated in your question is appropriate for generating uncertainty for THIS kind of measurement. But you should also know, it's a very bad rule. To see why, consider:
[tex]
f(x,y) = x_{\hbox{\small best}} + y_{\hbox{\small best}} \pm (\Delta x + \Delta y)[/tex]
This assumes the WORST CASE SCENARIO. It assumes that you made a measurement of x, and got the worst possible measurement. But even worse than that, you made a measurement of y and also got the worst possible measurement. But even worse still, your errors in x and y were in "the same direction". There's a good chance that x might have been an overestimate, and y an underestimate, producing cancelling errors. But by adding [itex]\Delta x + \Delta y[/itex], you've assumed that both were complete overestimates. Or both were complete underestimates, with no cancellation of error.
For this reason, when computing the sum or difference of measured quantities, you should add the error estimates in quadrature, not direct summation.
I've given you more than you've asked for. Hope it didn't confuse. Do look into the Taylor book. It's really, really good.