The traditional statistical analysis of your five observations would be
rather different than a physicist's 'error analysis'. Here is the usual
terminology of the statistical analysis, along with methods of computation.
The statistical analysis assumes that the measurements are a random sample
from a normal distribution with unknown mean $\mu$ and standard deviation
$\sigma.$
Confidence interval. The usual statistical approach would be to find a 95% 'confidence interval'
for the true period of the pendulum. In R statistical software, this interval can be computed as shown
below. I use the notation $X_1, X_2, \dots X_5$ for the five measurements.
(This is to avoid confusion with Student's t distribution, which is used in
finding the confidence interval.)
x = c(5.1,5.3,5.3,4.9,5.0)
t.test(x)$conf.int
[1] 4.897884 5.342116
attr(,"conf.level")
[1] 0.95
Rounded to two places, the confidence interval is $(4.90, 5.34).$
The computation is based on $\bar X \pm t^*S/\sqrt{n}.$ Here $\bar X = 5.12, S = 0.179,$ and $n = 5.$ The number $t^* = 2.776$ cuts 2.5% of the probability from the upper
tail of Student's t distribution (a distribution symmetrical about 0) with $\nu = n - 1 = 4$ degrees of freedom.
mean(x); sd(x); length(x)
[1] 5.12
[1] 0.1788854
[1] 5
qt(.975, 4)
[1] 2.776445
Standard errors. The 'standard error of the mean' is $SD(\bar X) = \sigma/\sqrt{5}.$ It is estimated
as $S/\sqrt{5} = 0.08.$ Because the population standard deviation $\sigma$ is seldom known, it is usual to use the terminology 'standard error of the mean' for
this (estimated) standard error.
sd(x)/sqrt(5)
[1] 0.08
Margin of error of CI. The margin of error for the confidence interval is the half-width of the confidence interval: $t^*S/\sqrt{n} = 0.222.$
qt(.975, 4)*sd(x)/sqrt(5)
[1] 0.2221156
Error of a single observation in the sample. If you really see an advantage in knowing the the standard deviation
$SD(X_i)$ for a single observation, that would be $\sigma$ estimated
as $S = 0.179.$ I see no sound statistical rationale for saying this is
"half the smallest digit on the digital stopwatch" because I can imagine
sources of error other than rounding.
Prediction interval for additional observation. If you want a 95% 'prediction interval' for an additional measurement $X_6$ (not used to
estimate $\mu$ by $\bar X$ or $\sigma$ by $S$),
that would be found as $\bar X \pm 2.776S\sqrt{1 + 1/5}$ or $(4.58, 5.66).$
pm = c(-1,1); mean(x) + pm*qt(.975,4)*sd(x)*sqrt(1.2)
[1] 4.57593 5.66407
Notice that two sources of error are involved here: error from the original
sample of five and the error of the new measurement. [If $\mu$ and $\sigma$ were precisely known (not estimated from five observations),
the 95% prediction interval for $X_6$ would be $\mu \pm 1.96\sigma.]$