Great concept, turning city builder into a puzzle works perfect as a game mechanic and fits the theme of the jam. Music and graphics work very well together and a nice polishing touch on the tooltips: they don't get in the way and explain the mechanics well!
If you are looking for any next steps to take this further, working on balancing would be the number one priority, it seems that too much is dependent on the random number generator. I too had a big issue with rolling for road tiles and could not proceed on the first play through but did much better on the second. One way to do it would be to analyse all the openings and ensure all the tiles can be placed and if the player messes up - introduce an undo action.
By adding more assets and little animation + levels in different biomes / geographies could very well lead this to be a nice full fledged puzzle game, well done!
Viewing post in Meadowside mayor (prototype) jam comments
Thank you for feedback. We've added some restrictions to tiles generator to ensure that it's always possible to play at least 4 tiles on hand if you've menaged to play all of the previous ones but our system is not perfect and if you're unlucky or unexpirienced than it still can be extremly hard to not lose. As you're the 2'nd person complaining about it we might change the tiles generator's restrictions to make the gameplay easier if we continue working on this project.