I think auto-roofing should be an option for sure, but I personally always had it turned off because it always placed the same style of roof, and they weren't nice looking.
Depends on house form whether I suse it, but a definite yes. As usual, TS2 does it right with the option to either auto roof with several types available or to go DIY with roof types. Also much prefer their provision of a specific angle. Way too much guesswork in TS4, especially where there are intersecting roofs.
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Roofs are very annoying to build, I agree, BUT I think that taking some time to figure out how to build one is better than allowing CPU to do it for player. The results may get even messier. I agree that to have the OPTION is good, but I am not sure it is good idea overall.
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I do think they should include it though, a lot of people would find this useful, just let us toggle it on/off.