While this might make some sense when it comes to the pie-shaped cul-de-sac lots, it seems to be happening within simple rectangles, too. You can't really blame the GIS program for not being able to draw curved lines in many of the cases. It just appears that the lines go through garages and living rooms. When I looked at my own neighborhood, this isn't really the case, and our lots are about the same size, so it's not like the mapping program has it wrong everywhere.
Let's just assume the property lines are wrong. These houses were built in the mid-1990s, and it seems the lines should have been updated in JAXGIS by now. I was taking GIS courses at UW-Milwaukee back in the mid-1990s, and the technology wasn't perfect, but even then there were ways to correct issues like these. However, I also know how long it takes to work with older GIS programs, so maybe that's the issue here.
It's also possible that property lines are messed up in The Woods. Maybe the HOA controls it so that there are no disputes, but I know from being a homeowner for well over a decade that disputes happen. If the last five feet of my neighbor's bedroom was technically on my property, I'd kind of worry about them jumping on their bed. I mean, when my neighbor slices his finger while cutting some wood in the garage, and it's on my property, can I get sued?
Sure, it sounds silly, but property lines in the wrong place are not a laughing matter to most homeowners. As soon as I left my Milwaukee house (listed for sale), the neighbor pulled out my garden fencing and added stakes to show her property line. And she's not the only one who would do that. In The Woods, are there people putting up fences that use the neighbor's dining room as a section of the border? Do you need to mow right up to your neighbor's house? Can you borrow flour any time you want because you own the pantry part of the kitchen?