Haha, thanks Reaper47. The reason I would build street for the sake of it is because all I want is my work to look like any run of the mill Valve map, or else they end up as some sort of freak show I try to mimic official maps just for the professional look rather than gameplay. The game play is build around the map in my maps, rather than vice versa. Brings back good old memories of the Snarkpit talks on here. The days of Orpheus and Leperous were good memories. Now the days of the new guard are good memories as well Thanks for the info about building stuff and then rotating it. Next time I am in that situation I will try to angle it with Vertex manip.

Building streets just to "build streets" is a bad idea, generally.

Always make sure there's an interesting shape and gameplay area. Something that looks inviting, a place you haven't seen in dozens of other maps before. Then make a few little sketches (the uglier, the better) of the area. In these, try to identify areas that are just long-winded, boring areas with nothing interesting to them. Condense them until you have something exciting literally around every corner. In fact, even the corners themselves should have something special to them.

Now you can start building.

Getting the right amount of detail to both get things done and not run into problems later from over-simplification is one of the hardest thing there is for a mapper. I'm still figuring that out. I usually try to make sure all walkable areas or gameplay/optimization relevant walls are exactly to-the-unit like they should be in the final version. Then you can cut out or add detail as you polish the map.

Sticking to a 16, better 32-grid is essential for something as big as an entire house! If you don't do that, you'll be screwed, soon. For skewed angles, use the vertex tool and snap all the edges to grid in there. Don't use rotate. In fact, never use rotate, ever, ever.

Ahh, been a while I wrote things like this.

No matter how grid friendly I try to be, something always ends up in the tiny grid sizes

You'll have a very difficult time rotating a finished building and realigning to grid ( unless it's a model, but even then your nodraw solids inside it would need to be fixed ).

Much better to approach it by building it in-place, using slope ratios and the clip tool, and then adjusting windows/doors etc to gridlines with the vertex tool. You'll still have to make compromises in sizing here and there but it won't be noticeable.

The more rectangular and "power-of-2" your layout, the more engine-friendly it is. Try and make your solids so that all the horizontal and 45 degree vertical hinting works properly, then tack on details to form protrusions etc. When you turn off details and props in visgroups, you should be left with a fairly simple system of solids. So the answer to your first question is that the streets and sidewalks are determined by where the visblocking of the buildings ends up, not the other way around