Some excellent points. Timing chain vs. belt, property taxes (didn't think about that one!), depreciation, electric windows vs. manual, would other car-like 4-wheel vehicles be included? Etc., etc.
See, it's not a simple problem, is it?
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Yes, a good approach is to look up tax and insurance rates and then look for cars with rates you can stomach. There are lots of hilariously cheap big engine cars in my area because of the additional cost. On the tax side, there may also be beneficial loopholes, like tax credit for vans and strangely enough SUVs for businesses. Basically the car itself is the last thing to consider. Saves you the heartbreak of discovering that your dream car comes with tender loving by the taxman.