Tenant Data Report
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I don't believe the original poster has any idea how "easy" it would be, nor any idea how many Quicken users would find such a capability useful.
I believe the number/percentage of Quicken users who use the Rental Property features is very low. And the number of Quicken users who have more than one Property or Tenant must be much lower than that. For that reason, I believe, over the years, Intuit/Quicken have shown very little interest in improving the Rental Property features, and I've seen no sign that will change.
[One apparent characteristic of the op's wish seems even less likely than the others; that is, the ability to print multiple attachments of tenant documents at one time. Since Quicken doesn't print multiple attachments at one time anywhere in Quicken that I know of, I doubt they will make an exception for Tenant document attachments.]That having been said (and remembering that the Quicken Rental Property features are not designed for users with many properties/tenants), it appears the original poster did not look very hard to find a way to accomplish his purpose: Quicken already has two built in mechanisms for creating tenant reports with much of the Tenant information (though managing the more complete of those mechanisms may be more effort than the OP would like to exert).
There is a Quicken Tenant List, which contains and will print a report showing the tenant name, property name, property address, lease-start date, rent amount, and tenant phone number (why they did not include the lease-end date, I have no idea - but asking Quicken to include that date in the built-in Tenant List might actually fly. Note though; not all tenants have leases, so no they don't have lease-end dates). The existing Tenant report is for ALL tenants at one time, not just one. No effort at all required to utilize this.
For a report with more tenant data, tenant information can be added to the Quicken Address Book and printed from the Address Book (including, with proper preparation, sorting on lease-end date).
In each of the "Add Rental Property Tenant" and "Edit Rental Property Tenant" dialogs (where tenant information is captured by Quicken), is a button to "Add to Address Book".
While clicking the "Add to Address Book" button only automatically enters the tenant name to the Edit Address Book dialog, it leaves the Edit Address Book dialog open so the user can fill in whatever other Address Book fields are desired. Data from the Add/Edit Rental Property Tenant dialog (or virtually anywhere in Quicken) can be Copy/Pasted into the desired fields in the Address Book.
The user can create a new Quicken Address Book "Group" (named "Tenants", for example) with only the address book columns of the user's choosing, then assign Tenants to that group.
The Quicken Address book has some fields that can be used for just about any purpose. For example, there are three "Miscellaneous" fields, each with plenty of space for holding a date.
Using one of those Miscellaneous fields for the lease-start date and another one for the lease-end date provides the lease period information for a report. And choosing the format CCYY/MM/DD for those dates, will allow the user to sort on the appropriate Miscellaneous column (by clicking on the column Heading text) to see tenants in lease-end-date sequence.
With only the (new) Address Book "Tenants" Group selected, and the tenants sorted by the appropriate Miscellaneous column (the one containing the properly formatted lease-end date), a lease-end date report can be created.