Not sure if I understood what you mean but when you say you want to drill down from a large scale to street level, if you mean you'd like a massive project that lets you have all that scale in one map I know some version of Rebelle have a nanopixel feature where you can draw at one scale, then export it at a much larger scale, and it interprets it to avoid pixellation so you could then illustrate in more detail. If that was your question and I'm not misunderstanding, that might be a solution? It's not the cheapest option but there may be other software that can do the same thing.