I think you are saying "meanings" where I would say "values". So you want to find the set of values of x for which [MATH]f(x)\le 0[/MATH].
The tricky part here is that when the base of a logarithm is less than 1, the log is a decreasing function; since it is here being multiplied by a negative number, your function f is an increasing function, as shown on the graph.
In your work, you first divided by -3 to obtain the correct inequality [MATH]\log_{\frac{1}{2}}(x+8)\ge 0[/MATH]. But when you then eliminate the log, in effect by raising the base, [MATH]\frac{1}{2}[/MATH], to the power on each side, this reverses the direction of the inequality, because [MATH]\left(\frac{1}{2}\right)^x[/MATH] is a decreasing function -- that is, as x increases, this decreases toward zero. So now you have [MATH]x+8\le 1[/MATH], and the solution is [MATH]x\le -7[/MATH]. However, x must also be in the domain of the function f, which is [MATH]x>-8[/MATH]. Combining these, the actual solution is [MATH]8<x\le -7[/MATH].
I'm not sure what you are saying at the end about x=5. I'm wondering if the work you show is not really your work, but perhaps corrected according to the provided answer, and you don't understand it. For x=5, we find that [MATH]f(5) = -3\log_{\frac{1}{2}}(x+8) = -3\log_{\frac{1}{2}}(5+8) \approx 11.1[/MATH], which shows it is not in the solution set. Did you think it should be?