Hello, I have read your project description and more details would be necessary. I have experience with creating similar set of drawings in different countries and the main principle is pretty much the same, however each city has its own specific rules and requirements so you would need to check first what is required (only street elevation and site plan, or maybe all plans, site plan and all elevations, etc).
The set of drawings usually contains existing and new 'situation'. Existing state drawings are usually created based on sketch with measurements and photos. After that, based on your input and requirements, I would prepare 'new state'.
I usually send pdf once or twice so you can see the progress or/and in case there are additional questions and after your feedback make necessary changes.
Final files deliverable as dwg and pdf (with title block ready for permit application).
If you have any questions, feel free to contact me.