With the location selected, let's get started!

To start off, we need resources.

We need to set up: A Quarry, A forest to deforest, a place to gather sand for glass,
People gathering aesthetics(flowers, lilipads, etc), and people to help me terraform the area.

I'm down to chop down wood, but first we should set a block pallet to make the town look like it's a real town and not a bunch of different houses made out of different materials all thrown together.

What type of wood are we gonna use, what type of rock/stone? What are the roofs gonna be made out of?

We should also consider that the city needs to look good with the vanilla textures, so even if in your texture pack, birch wood looks gray and would suit the original style better, in reality birch is a yellow-ish white so lets not use that.

I suggest oak wood, cobblestone and normal glass panes. Now for the roofs, we have a difficult choice to make. In skyrim, the whiterun houses look like they have golden tiled roofs, but it would be impossible to gather that much gold to make the roofs and let's not forget that blocky roofs are ugly. We also could use yellow wool, that's more managable, but then again: blocky roofs. We could use hay blocks, but the roofs of the city are distinctly not made out of hay, so that's a lore-breaker if we want to stay close to the original. Now for stair options, we have birch and sandstone, both are meh, but could potentially look good if we revise the whole block pallet. The last option is, of course, to just make it out of something else like cobblestone and not care about the real thing because after all it's just a game! And of course gravel for paths.

I'll help with the quarry.

Go to my portal in the nether that leads to my house, and there is a huge birch and oak forest. Also, there is lots of spruce by spawn. (Not sure where to find other wood types, im sure the map would help.)

I got a whole bunch of sand today for the project. Netters

I know where to find a dark oak Forest if anyone wants to go gather it.

I have a but load of spruce wood