Using master equation and quantum Monte Carlo wavefunction approaches, we study the circumstances surrounding the emergence and degradation of the elusive squeezing of fluctuations in two-level atom resonance fluorescence. For its measurement we suggest conditional homodyne detection (CHD) [G.T. Foster, L.A. Orozco, H.M. Castro-Beltran, H.J. Carmichael, Phys. Rev. Lett. 85, pp. 3149-3152, 2000], which is nearly independent of detector efficiencies, which have harmed previous attemps. Squeezing in resonance fluorescence requires a weak laser, so the average interval between emitted photons is much longer than the regression time to the steady state; here, the spectrum of the out-of-phase quadrature is a negative peak. In CHD, moderate fields generate a non-zero third-order correlation in the dipole fluctuations that contaminates squeezing, making the noise nonGaussian. If the probability to emit two and even three close photons is still small the additional contribution is also negative, helping to make the full spectrum a bit larger and easier to measure. Strong driving spreads the photoemission distribution, which destroys squeezing, and the third order fluctuations become responsible for the non-classicality of the fluorescence.