hi, srry this is a bit late. first, very excited to see this spiffed up! one of my favorites.
alas, my first go produced this:
14.5 kB
i don't think there's any way to advance that town. i have a disturbingly huge sample size of games (lol i played this a lot!) and none of them did that before.
also... i'm not really keen on how the windmills animation goes now? i know that's a nitpick but the previous animation was not jerk-y reality-glitch. the still pixel art might be neater but in motion it kind of interrupts the vibe.
i'd also humbly suggest a few adjustments in resource requirements, as usually you don't pay much of a resource X to build the thing that makes resource X. most of the game mechanic nails this; but in many cases, like with population, it's grindingly unbalanced. i estimate you need about 3 houses to achieve steady population growth, and with the cost list of each house ... ironically it's difficult to actually attract settlers.
what might put this over the top into legend mode would be more area effects bonuses, like woodcutter next to forest (or type of tree! i've farmed maps into one type of tree, just for the Aesthetic. mushroom farms are my favorite too.) or house next to apples or sheep next to open grass.