Section 8 Cash for Keys - how much to offer?

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In cities with very pro-tenant leanings, eviction is long, expensive, and near impossible (especially in DC). If I were needing to change a tenant on a month to month lease, what would be a reasonable amount to offer as Cash for Keys (assuming a high cost area like DC)?

Also, how does the transaction take place?  Do you offer cash once they move out?  Half cash at agreement, the other half paid at move out?  I’d value any input. Thanks!