Your property might be legitimately worth $1,500 and the tenant qualifies for $500 in assistance, but can only afford to pay another $500 for a total of $1,000, they won't approve $1,500.Unfortunately, you can usually only find both of these out when you have an application and lease signed from a prospective tenant and submit it to the local housing authority.

The lease is not up for a couple years; however, the USPS has submitted a proposed lease to me for the next 5 years.

Now if this tenant would have simply submitted a work request we'd likely have fixed it.  

Assuming their insurance company refuses to pay, you can try submitting their expenses to your insurance company and see if they will pay.

Our project is raw land development so we're submitting everything all at once.

This is what I did for a cabin I built in Gatlinburg:  We took a few royalty-free photos of the area off of the internet, and submitted them to an art site online whereby they make a painting of the photo.  

Last question, you are hiring an architect and submitting plans to the city in a renovation like this correct?

I've submitted a report to the FBI and encourage everyone to do so as well. 

They will tell you to submit your request in writing and give you an email address or mailing address.

I'm about to rent out my first property and would love a recommendation on an app to use to screen applicants, submit maintenance requests, and receive rent.