Back in the 1990s when I started my investor career, “bootleg” or illegal structures, constructed in a workmanlike manner, were not scrutinized like they are today. As long as the appraiser didn’t use the illegal structures in value calculations, the lender seemed to look the other way. Fast forward to today and, in my opinion, illegal structures are a liability and detract from the property value. More and more cities are requiring pre-sale inspections that flag bootleg additions. Also, appraisers are more likely to call out discrepancies in bed/bath count and square footage. Having legalized many seemingly well-made bootleg additions, in retrospect, it would have been cheaper to tear down and build fresh. Legalizing additions means complying with the planning and building department. The structures will need to meet setback and zoning requirements. After that hurdle, the fun begins. Bootleg structures will need to meet current building codes. The city will probably require architectural and engineering drawings. The field inspector will ask for the opening up of footings, walls, and ceilings to verify things like rebar size and spacing, sheer wall, framing, etc. At the end of the day, it’s a considerable investment of time and money that many sellers need to be educated about. Buyers need to make sure their offering prices take this into consideration.