Wondering about the entire process, from gathering permits (if necessary, and would love clarity on this), to executing on the project. 

Funds permitting, I set a goal for 5 SFR's in the next 3 years and see which direction I'd like to take investing from there on. 

I'm assuming, given the scope, that this is going to be a requirement for permits/the building department.

I verified all of the needed information (taxes, flood zone risk, insurance, permits, septic / well information, tree trimming, budget estimates for a new roof...).

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.