they can't figure out how to dynamically adjust the typeface of the 12 characters in "MLK Jr. Blvd" so they stay visible as I zoom in and out on a city neighborhood?
This seems to be quite complicated. I have experience labeling maps with QGIS, ArcGIS online, and UMN mapserver, and it's kind of a PITA in all cases. It took me quite a bit of thrashing around with QGIS to come up with a map labeling style which actually checked every box, and never really got there with the others. That is, roughly:
All labels both legible and not obscuring anything
Full names of all visible streets shown
No label is closer to a street it isn't labeling than one which it is
Labels repeat only at useful distances along a street
Sidebar: QGIS is super duper cool, I have come up with a pretty nice map which has got parcels and whatnot when you zoom in, all from public data. As you get closer, more features and data appear. The latest US Census TIGER dataset is a very good practical starting point for this country, but there are lots of other sources.