This is a great question! It think you'll find Chapter 25, Section 2 of the toolbox to be helpful in thinking overall about the process of assessing your neighborhood/community.
For a specific tool/checklist, you might look into work in the area of public health that seeks to understand the impact of the "built environment" on health. I did a quick search for "neighborhood observation" and came across a couple of things you might find helpful:
http://www.hepdetroit.org/37-hep/data-collection-activities/262-neighbor...
- This one had lots of information, but the link to the actual checklist didn't work when I tried it. You might try contacting the organization for more information.
https://activelivingresearch.org/active-neighborhood-checklist
If these don't fit exactly what you're looking for, they might at least give you an idea of how to develop your own tool, tailored to your needs.
Good luck!