Currently, I have shoes in the low (Loakes), mid (C&J & Church's) and higher (EG) strata in my collection but have yet to decide which are the best value to me (meaning which brand I would buy again should I need to replace some existing shoes).
For me, I would assess my shoes for (1) comfort, (2) longevity and (3) asthetics.
Comfort will mostly depend on the last and sizing but certain construction factors (e.g. the smoothness of the seams inside the shoe) also matter.
Apart from the fact that higher-end shoes having oak bark tanned soles will probably have better longevity per soling, low-end shoes will most probably last as long as higher-end. However, as I Topy all my shoes the sole leather durability will not be important to me.
For asthetics, I do not value the minor detailing that cannot be seen more than a few feet away. However, I would expect the more expensive shoe to look better throughout its life as the higher quality leather upper will crease less and probably polish better.