Always instruct your tenants to go to the RESIDENTS page on your website. On your website they can fill in the blanks and attach photos of their repair request. When they hit the submit button, it is auto-emailed to you. Now you can attach everything in this email to their tenant record in your Tenant Tracking company file.
Work Orders are your golden opportunity to have your handyman, service technician, and all of your licensed trade vendors to be your eyes and ears. Groom them to be observant and look for things that don't look right. Here's what is required on all of my Work Orders. It does not matter if it is in-house or assigned to a vendor.
Tenant reports blah, blah, blah. (After this, you will enter each of the following tasks)
Now this is very easy on the eyes and whoever is doing this Work Order has a very clear understanding of what needs to be fixed.
On top of this, whoever does this Work Order must take photos of: