Once the big stuff is opened up and no major setbacks found, all else can procede as planned.

County records will be adjusted, and you will add value that can be documented.I know people that have purchased property that had (extra) rooms built to the house, and that have even had garages 2' over a lot set-back line, only to have to remove these illegal repairs soon after the purchase.

Title Transfer and other regulatory paperwork - are these typically taken care of by the agent during the transaction, and are there ways to verify the title has been transferred to the correct party?

Corner lots: This allows you to be creative with what is the "backyard" and what is the "front yard", which helps with placement of the DADU and setbacks.

Some custodians do have internal polices that where they choose not to process certain transactions that can lead to greater complexity in account management such as foreign real estate or UBIT creating trade or business activities, but that is a business model decision, not a legal restriction they are confined by.This lack of oversight is a factor of the regulatory environment, not their service attitude, by the way. 

Must haves are:1) Contractor connections2) Regulatory knowledge, especially a pulse on what’s coming in the future (at the county, town and HOA level)Bonus points if you understand yield and how to underwrite deals.

Taking on extra regulatory risk anytime you buy in an HOA.

After yrs of setbacks and a little FOF/FOS, i am finally able to jump in and get going on my Real estate path.

., you will want to talk to the Planning and Building Departments and find out the what is required for setbacks, driveways, sidewalks, landscaping, height limitations, etc.

How is the regulatory landscape for STR around Orlando?