Finally got the Street scene done complete with UV mapping. Took a long time, but is pretty satisfying once everything starts to fall into place. I hope everything turned out fine with the UVs as I had to fix some rogue one's floating about.
Windows + Door UVs
Front facade UVs
I also found the solution to my earlier problem of bevelling after committing to some extruding, turns out I had 'Keep Faces Together' off causing some problems. Not to fear, as I patched up any faces that went awry after extruding with some merging.
I'd like to think I'm getting better with each task, being a bit more efficient successfully solving some rogue problems. Though, I think time will surely tell when we start creating our own dictated objects.