Honolulu County Non-Conforming Single Family Purchase

[Anna W.]

The market here on Oahu has so many non-conforming properties that have say an extra wet bar or extra non-permitted bedrooms. We want to but a primary home property with either VA, traditional or FHA depending on the property and what we can do with it. The DPP process for building an ADU is not too complicated, but how should we choose a property based on those guidelines not knowing for sure if we will get permitting approved in the future? Has anyone bought a non-conforming and successfully renovated it with proper permitting? We're looking at a property between 7 and 8,000 sq. ft. lot with an extra non conforming bedroom and bath. I guess i'm mostly looking for success stories in either building a permitted ADU with approximate cost figures, permitting a non-conforming to a conforming multi family or duplex, and just how do you even start? We've only purchased a duplex and condo before, so unfamiliar with all the red tape. We are from Oahu though so at least familiar with the lay of the land and pricing. Thank you!