one of my friends learned how to play guitar on a classical with a 2 1/8" nut, flat fretboard &
'mile-high' action. he teaches & is an absolute whiz on a Tele, along with steel string acoustics,
so i would subscribe to the theory that the more difficult a guitar is to play, if one becomes
proficient at it, then a guitar set-up with lighter strings & lower action will be easier to play,
provided one continues to stick with it & that there are no issues that develop (carpal tunnel, etc)
using medium strings to build up strength make playing with lights easier could work, but it may cause some
difficulties, as one may try to fret the light strings with the same effort as mediums, which can also affect tone -
i've rarely used a full mediums (.013, .017, .026), as i prefer the tone & feel of .012, .016, .024, so i use EXP19s
i'd suggest playng what is most comfortable & then looking at stepping up
the gauges, if the tone desired comes from using those heavier gauge strings
ymmv