If so You need to hire a design build contractor or an architect to develop plans and specifications to start moving forward with the project and permitting process.

Just to get permits for pylons and retaining walls will take 8-10mos... plus roughly $100k just for that.    

Just call down to the zoning, code and permitting office at George St and ask them the specifics.

I was at the building permit office today and inquired what I would need to show in order to get the permit approved.

There is one slight issue, the property has an open permit from 1992!

They will tell you the next steps which likely will involve DOT in your area depending on where the property is located and what type of street or highway you are on.Assuming you can proceed the next step is to hire a civil engineering firm to do all the survey work, site plan, actual construction details, traffic studies if needed and help get all the permits for you etc. 

That sounds like a more elaborate version of what's happening in Nashville, namely, condos that are appropriately zoned and STR-permit eligible, with HOAs that explicitly allow STRs.  

I have a detached and permitted ADU (400 SF) which currently is a Studio.

We'll pay for permit and dumpster, then funds come after work completed weekly/biweekly as stated.

You could get the city involved as they may stop any work/permits they may have planned.