Alert Based on Field Value

If I put a Custom Entity record's status reason field to "On Hold", would it be possible to alert the owner of the record after a specified time? One example: create a new field called "Remind me" with options "30 days", "60 days" or "90 days", which would run a workflow to send an email to the owner of the custom entity record after the specified time? 

I imagine a route to implement would be to have an "On Hold Expiry" SSRS report.

Any help is appreciated.

Thanks,

Blayze