Defining the optimal sampling time across the growing season is crucial to standardize sampling protocols for soil physical status monitoring and to achieve comparable results under different experimental conditions and on different sites. In this study, the seasonal variability of soil physical and hydraulic properties under two conservative soil management strategies, minimum tillage and no-tillage, was evaluated in a long-term field experiment. On two sampling dates, autumn 2021 and summer 2022, soil bulk density (BD) and volumetric soil water content at the time of the experiments (θi) were measured in each experimental unit and Beerkan infiltration experiments were performed. The soil water retention curve and the hydraulic conductivity function were then estimated using the Beerkan estimation of soil transfer parameters (BEST) methodology. In this way, the saturated hydraulic conductivity (Ks) and a set of capacitive indicators—plant available water capacity (PAWC), soil macroporosity (PMAC), air capacity (AC) and relative field capacity (RFC)—were obtained. Results underlined the role of soil moisture conditions as a main factor affecting variability in soil physical properties. Different soil moisture under autumn and summer samplings significantly affected BD (1.0093 and 1.1905 g cm−3, respectively, in autumn and summer) and Ks (0.0431 and 0.0492 mm s−1). Relationships observed between BEST-derived variables, such as PMAC (or AC) and RFC, and measured variables, such as BD, showed consistent results, with increases in PMAC to BD decreases. However, a comparison of capacity-based indicators obtained by BEST with those obtained from measured soil water retention curves, in a previous year but under comparable soil conditions, highlighted some discrepancies. This finding drives the focus towards the need to use more robust datasets deriving from experimental measurements or from coupling information obtained from measured and estimated data. Finally, this study provided further evidence that, in the long-term field experiment investigated, the two soil management systems allowed keeping the values of key soil physical quality indicators, such as bulk density and saturated hydraulic conductivity, within the optimal or near- optimal reference ranges.