compartment syndrome is rare, rare and rare. it is the last diagnosis for shin pain.
can clarify the location "left side of the shin bone as you look at it" who is looking at it?? maybe say the outside (lateral shin) or inside (medial edge).
MTSS is no doubt what you had before "shin Splints" most common cause. caused by flat feet - however old shoes where down and eventually give little support the the inside arch of the foot, hence why this is related to shoes getting old.
your current condition is different and is most likely caused by you changing your running style. in both incidence where you where getting the pain. hill running and speed running a athlete changes there gait. essentially hill running will give little rest to the muscle located in the front of shin and a sudden change in running can cause poor acquisition of technique. running for speed might have forced you to toe off excessively.
get your gait check - job done.
also you can rule out MTSS with a foot analysis and some palpation - easy,
hope it helps






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