Cal may prefer playing a shorter roster at the end of the day, but he also likes to pull players and use the bench as a motivator to make sure players play the way he wants them to. Without much depth, he loses that option. And although the 2013-14 team was deep, there were some spots (such as James Young and the twins) where at times Cal would probably have liked to utilize the bench but couldn't because he didn't have other viable options, and it showed in his frustration. The 2012-13 team was another example where Cal got visibly frustrated not being able to freely sub key players (Harrow for example), and in the end this lack of depth ended up biting the team. And remember this is what prompted Cal to say he would never be caught short on depth again.
Frankly when Cal was running full platoons early in the last season he seemed to be at his most relaxed I've ever seen him, as UK was kicking tail and he really didn't have to spend much time thinking about making substitutions, but rather could concentrate more on coaching the game in front of him. That's one (of many) reasons why I thought that platoons was perfect for last year's squad (at least until Alex got injured). And Cal even commented a few times how much easier it was to coach during that time.
But the more the season progressed and the more he went away from platoons the more he reverted back IMO to a more frantic Cal, who endlessly tried substitution pattern after substitution searching in vain for a 'perfect' combination, even though UK's efficiency dropped the more he tinkered.
Given the above, I think in terms of choosing who to play, it will be easier managing the team, but that likely doesn't translate into a better result on the court, or a less frustrated coach. The opposite in fact. Also given the short roster, this team has little to no margin for error in terms of being in contention for a title.
Given the above, I'd rather have a deep roster any day.