It's definitely taking shape! Great stuff yet again!
I think you're right that things will start to gel more when the economics settles in.
How are you structuring the concept of accumulated "wealth" per individual? At the moment it appears that they all just build houses and this is fine if your 10 Andys represents more than that. If not then the housing price would be at rock bottom by the time of this end screenshot! You have a lot of very poor Andys!
I'm not sure building decay is necessarily the right mechanism for creating space for roads. I would suggest that the buildings would not be built in the first place? Keep it at one building per Andy and have different sizes (wealth) perhaps? In other words have 2 sheds by all means, but make them joined together and cost exponentially more?
Other things to throw into the melting pot? You've probably thought of these already?
What does a "community" usually build early on? A church? A marketplace? A community hall? A pub? People are a sociable bunch so you could consider building in such things. People also need leisure time and meet each other... a certain amount of "need" should be doing these things. Visiting other people's houses, going to the community building and so on.
I'm also thinking that to support this your Andys should choose a "proffession" rather than be Jacks (of all Trades!) which sets up your trade system. (This doesn't necessarily negate trade between two stonemasons, they just specialise in different types of rock, no need to model that just put that sort of trade as lower "need" perhaps.) Trade requires "meeting" at one or the others house or market, which means that people can't be out all day chopping trees, they also have to sell... and that's what shopping hours/market days are all about. I've worked in shops (jewellers as a matter of fact = rocks!), you can spend a lot of time doing nothing waiting for someone to buy something.
What criteria are used to decide where to build a house? Once someone's profession becomes, say, lumberjack, and all his other needs are bought then he wants to be close to the forest and "the shops"/market, he no longer needs to be near the stone field or any other raw source of "commodities"...
You also probably need to stick in some "logical thinking" - once a road becomes established enough and long enough then building next to it is far more logical.
Many towns are created just because the road was there and a commodity was there. I was brought up in just such a town, built on the old roman Watling Street (A5) and a good spot for clay and therefore a pottery...that's a theory anyway! A fair amount of your building "boom" seems to be "infill"?
Anyway, like I said, I'm just throwing in ideas here!
Keep it going!