Solo Operator: Need a "Clean" Reporting Workflow in ClickUp (Monthly Inspections/Maintenance)

Hey guys! I’m a solo operator doing monthly maintenance for Short-Term Rentals (descaling, filter changes, etc.). I’m trying to see if I’m overthinking my ClickUp setup or if maybe there is a decent solution for what I’m wanting…

My Goal: Unique checklists for each property with "Proof of Work" (photos/comments) sent to clients monthly.

Current Setup:

• Each property is a task. Subtasks = the tasks I perform on a job site.

• I use task templates for each homes unique checklist and schedule frequencies.

• The Problem: I currently take photos on my phone -> upload to Dropbox -> comment on photos -> create a manual PDF for the client. I’ve been curious if I can accomplish all of this in ClickUp and yet make it easy in th client (not signing up for an account, etc.)

Problems I’m seeing so far:

1. I want to attach photos/notes to a task and share that specific "visit" with a customer.

2. The Recurring Task Issue: If I use a "Files" Custom Field, the photos from January are still there when the task recurs for February. I want a clean slate for every visit.

3. If I attach photos to subtasks directly, there’s no easy "column" for the customer to see them in a Table view.

My specific questions:

- How are you guys handling "Proof of Work" reports for clients without manual PDF building?

- Is there a way to have attachments "clear out" on a recurring task, or should I be creating a new task from a template every month instead of using the "Recur" feature?

- Has anyone successfully used ClickUp Docs or Dashboards as a client portal to show only the most recent completion?

In life I really do tend to over complicate things… this is a small business and I don’t plan on scaling past 15 properties a month - but just wanting to streamline anything I can… open to any comments or ideas.

Thanks!