Thou shouldest not haue entred into the gate of my people, in the day of their destruction, neither shouldest thou haue once looked on their affliction in the day of their destruction, nor haue layde hands on their substance in the day of their destruction.
Obadiah 1:11 When thou stoodest on the other side, in the day that the strangers caried away his substance, and straungers entred into his gates, and cast lots vpon Ierusalem, euen thou wast as one of them.
Obadiah 1:12 But thou shouldest not haue beholden the day of thy brother, in the day that hee was made a stranger, neither shouldest thou haue reioyced ouer the children of Iudah, in the day of their destruction: thou shouldest not haue spoken proudly in the day of affliction.
Obadiah 1:13 Thou shouldest not haue entred into the gate of my people, in the day of their destruction, neither shouldest thou haue once looked on their affliction in the day of their destruction, nor haue layde hands on their substance in the day of their destruction.
Obadiah 1:14 Neyther shouldest thou haue stande in the crosse wayes to cut off them, that shoulde escape, neither shouldest thou haue shut vp the remnant thereof in the day of affliction.
Obadiah 1:15 For the day of the Lord is neere, vpon all the heathen: as thou hast done, it shall bee done to thee: thy reward shall returne vpon thine head.
The verse centers on "thou", "shouldest", "haue", "entred", "gate", "people", "destruction", and "neither". It is saying that the verse draws attention to "thou" and "shouldest", so its meaning should be read from those terms before moving to application.
The nearby context moves from verse 12's "But thou shouldest not haue beholden the..." into verse 14's "Neyther shouldest thou haue stande in the...", so "thou" and "shouldest" belong inside that flow. In Obadiah context, the local focus is covenant, worship, and faithfulness.
A plain takeaway is to answer the verse's own emphasis on "thou" and "shouldest" with trust shaped by these words, not by a vague optimism outside the passage.