The decline of relative chlorophyll contents during fruit ripening is considered to be an important indicator of fruit physiological condition. The recent availability of low-cost portable visible spectrum (VIS) spectrometers has spurred research interest towards optical sensing of chlorophyll changes in intact fruit, with many scientists attempting to link the shifts in optical signals, attributed to chlorophyll changes, to different maturity and quality parameters. One of the widely available portable devices for non-destructive estimation of relative chlorophyll contents is the DA meter, which provides a maturity index that is calculated as a difference between absorption at 670 nm (near the chlorophyll-a absorption peak) and 720 nm (background of the spectrum), abbreviated as IAD. In the present study, the evolution of IAD and its relation to starch pattern index (SPI) and fruit flesh firmness (FFF) was monitored in fruit of two cv. ‘Gala’ clones during maturation and storage, aiming to identify a potential existence of a usable IAD range for the assessment and prediction of the optimal harvest window and storage potential. In both clones, canopy positions, fruit sides, and seasons IAD, SPI, and FFF generally changed in a linear fashion over time, but with partially very different slopes, i.e., they were changing at different rates. What all of these parameters had in common was the presence of a very high biological variability, which is typical of apple fruit. Significantly powerful estimations of SPI (r2 > 0.7, p < 0.005) and pre- and post-storage FFF (r2 > 0.6, p < 0.005) were achieved. However, the very large biological variability could not be neutralized, which means that the predictions always included large confidence intervals of up to 0.46−0.59 units for SPI and 0.82−1.1 kgF FFF, which ultimately makes them unusable for practical applications. Experiments done under real-life conditions in a commercial fruit storage facility on several different fruit batches confirmed that IAD measured at harvest cannot be used indiscriminately for predicting post-storage FFF of cv. ‘Gala’ originating from different orchards. Nevertheless, mean IAD values that were obtained at optimal maturity from samples of the same orchards remained stable over seasons (0.8−1.2), which strongly suggests that, provided that the calibrations and validations are not only cultivar, but also orchard-specific, IAD has a potential for estimating maturity and storability of apple fruit. In this case, IAD could replace standard maturity indices, otherwise it would be suited for use as a supplementary index for determining fruits physiological maturity status.