I've been working on this in my free time for a while. It's largely based on the Jeanne dArc apartments in NYC. I'm at the point where I seem to be hitting some bumps in my workflow and could use some advice on the best way to continue.

I've been carefully modeling on a grid in Max to keep all of my bits and pieces nicely tileable. I want to keep things modular so that I can construct other buildings from the parts.

In my test export to UDK things are looking good scale-wise (please ignore lack of lightmaps), but I noticed that simply tiling my brick pattern on boxes doesn't look great. The grout gaps wind up on the corners, so I decided try to create a model with proper end pieces to bake maps from.

This is where I seem to be spinning my wheels. After a lot of trial and error, and researching I have a normal map that is approaching acceptable. I added a lot of edge loops and bevels to my low poly so that I could get a better bake that I then plan to use on a simple box (Is this a common way to do things?). I had the idea of creating a tileable texture from the middle of this map, but I'm not entirely sure if this is practical. I also plan to add some chips and noise detail to my normals in photoshop with the xnormal plugins.

I would greatly appreciate any feedback on my process. I feel like it needs some serious tweaking.
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Also one of the best ways I've found to do a tiling map like this is to offset your bricks nicely and then duplicate the high poly in all four directions (aka tile it) and then bake down to a plane you have positioned in the center square. If done correctly it should yield a perfectly tiling map, if done wrong nothing a few minutes in PS or a re-bake can't fix rather easily.
I still want to have a version of the wall with end pieces so that the corners look correct. I think I can simplify my low poly and still get an ok bake. I'll do a little more experimenting with that tonight. I imagined my corner pieces blending in seamlessly with my tiled bricks. This might be a pipe dream. Additional tips would be appreciated! I'm getting a little burned out on the bricks. Want to move forward!
Also, for the corners, I would recommend you use a different larger brick (I recommend white) and put it on the corner pieces. You can see some examples of what I mean here: http://images.wikia.com/assassinscreed/images/8/89/Assassin's_Creed_Brotherhood_Concept_Art_009.jpg
I'm not certain if Mudbox has a similar feature but in Zbrush I isolate each brick within the sculpting program ( CTRL-SHIFT + Click in Zbrush) I sculpt each brick on it's own, but this method allows them to stay in their already tiling formation. Maybe someone more familiar with Mudbox can explain if there's a similar feature there as well.
As for the corner pieces, it'll depend on the actual geo but you should be able to create something that blends with the flat pieces. It'll just take some careful unwrapping to make sure the edges line up.
Did a little test and I can get the whole wall into Mudbox and sculpt in a manner similar to what you are talking about, Xelan. I'm just not sure where to go from there. Should all of this geometry I'm creating go back into Max or xNormal for baking, or is that something that's usually done in the sculpting app in this kind of situation?
If you want this to be a nice continuous normal, that you can use other places than just this mesh, I suggest the champher route so you can keep the UVs in one piece.
I also noticed that I forgot to pad the top and bottom rows of bricks so that my AO baked out correctly on the tiled version. You can see it as a lighter horizontal line of grout in the image above.
Beyond this, it's quite a unefficent way of using a brick texture. The corner grouting is something you probably won't look at very often, creating a separate texture for something that is shown about a fraction of the rest of the scene isn't very smart usage of resources. Of course a scene wouldn't fall on something like this, but something to take in consideration.
But for a study of smoothing groups vs tangent normals, yes.
If you want a soft edge with a tiling texture and inhibit some sort of edge effect, you can work with your smoothing groups to do so as well.
In reference to splitting the uv shells, wouldn't I get ray misses where the grout is inset? It was the reason I beveled the corner initially.
I hadn't considered the mipmapping concern before. Would it be a problem to have the top and bottom of my shells touching the edge of the uv space?
In max, giving surfaces smoothing groups doesnt create the actual split physically. You have to create the split yourself (my bad).
If you have a tiled textures, flushing it to the "borders" of your uvw, is just good. However, if you have a individual asset, flushing edges to the might give some odd mip mapping issues, but it depends a bit on the geometry aswell. Just keeping away 2-4 pixels and giving the same amount of padding should be sufficent.
Anyway, here's a window texture test. Not sure I'm going to stick with these particular curtains, and I plan to do several variations.