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caffeinate
A Rails engine for drip campaigns/scheduled sequences and periodical support. Works with ActionMailer, and other things.
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InfluxDB
Power Real-Time Data Analytics at Scale. Get real-time insights from all types of time series data with InfluxDB. Ingest, query, and analyze billions of data points in real-time with unbounded cardinality.
Caffeinate might cover your bases: https://github.com/joshmn/caffeinate
Another option is to dig into the Sidekiq scheduled job set if/when the loan end date is changed (which you can detect via a Rails after_commit hook and then by checking the model's previous_changes), delete the originally scheduled job, and schedule a new job for the appropriate time. For example, the hired/reactor library implements its watch option in this way; see relevant code here and here.
Related posts
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Rails application architecture for a marketing campaign creation module (e.g. to create logic where upon action A being performed by a user, event B will trigger in 7 days, and event C in 14 days, etc)
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Caffeinate: A Rails engine for scheduled email sequences (/r/rails)
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I just released a gem that makes it easy to automatically unsubscribe from emails in Rails ?
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Caffeinate: A Rails engine for scheduled email sequences
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Mautic - How Open Source Shapes Marketing- Open Source Project Spotlight