@FinHermit , I can get my population up to around 360-375, but then it begins to crash. I have multiple kinds of food, multiple kinds of services, an usually a majority of overlap in grocers, an plenty of desirable locations (parks, squares, etc.) and higher-end goods (furniture, glassware, etc.). And it will run fine for maybe 3-4 seasons (with growth stagnate, but sustained). Then, it will cross over a winter into a new year and some 20-30% of the buildings will suddenly be at 33% level of maintenance - all needing either (mostly) boards from the sawmills, or (to a lesser extent), clay. In ALL cases, I have plenty of inventory of both when this happens - but there is no way to direct some one to address it.
Also, (and maybe related to the trading post), at some point, despite plenty of well-managed, timed, and staffed farms, the wheat just seems to disappear!!! This affects the miller, the baker, the brewery, and by extension, pubs!
And before anyone else asks, yes, I realize that many of the production shops require either/and tools and heavy tools, but again, I will have these in all places and extra inventory available!
There ought to be a selection on when you press the magnifying glass showing the the low maintenance, that the pop-up has the option to set the remedy to a priority just like any other build option.