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Are you taxing land, or are you taxing land value? If it's the latter, you can definitely lower the production of land value. I could make my house look super-ugly, put bars over the windows and cover the lawns in trash to reduce it's valuation. If you think you can decouple this as an improvement distinct from the value of the land itself... good luck.
People will deliberately uglify their homes to avoid taxes. The UK has experience with this, back when we had a window tax. Intended to be a simple way to assess property taxes - larger houses have more windows, windows can be counted from the outside, can't cheat the number of windows you have. People responded by bricking up their windows and living in darkness instead of paying the tax.
Land value doesn't stem from what's built on it but rather what surrounds it. You might uglify your own house to reduce your taxes, but the majority of that loss in land value (and hence reduction in tax) will go to people around you. There's a big collective action problem that would need to be solved for that to take place.
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The land value tax doesn't consider what your improvements look like. If you own a run down shack on an acre of land, and there's a skyscraper on an acre next to you, you're taxed the same. And this is meant to encourage you to rip down your shack and build a skyscraper, too, because the burden of paying tens of thousands a month in taxes is meant to penalize you for inefficiently using your land.
It's like how in Vancouver, BC, they brought in a vacancy tax and started taxing single story restaurants for not using the 'air' over their restaurant.
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Yes, assessment has always been an issue with taxation, going back into the dark mists of history. The idea is indeed to tax the value of land which, no matter how difficult the assessment, is still more efficient than other kinds of taxes as long as you're not trying to hit exactly 100% like the Georgists.
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