Hey Eric, hope this year is better to you and your family than some of the more recent ones.
As to your town's layout, I have the following ideas/suggestions:
The Billiards Lounge needs to be elsewhere, such as a corner, type of building. Maybe put the gazebo in this area, adjacent to the town hall, with some parking for 'downtown & the playground/town park.' After that, I'd relocate the two 'Queen Ann houses, further down the street, from where they are located, or elsewhere. I'm thinking maybe a bar/restaurant/hotel near the 'cable car station.' not to mention a train station in this vacinity, too. The town may have been laid out by a developer, with an eye towards everything being tied together, even if it wasn't all built at the same time-sort of like Vail, CO, or a few other places around.
Nearby the train station could be the cable car station, several places to eat/hang out, while waiting for the train, a hotel, maybe even the town hall, with the police station nearby to the keep the town's people 'orderly.' At the far end of town, where people live, not do business, would be the houses, etc...
Maybe somewhere, you can add a siding or two, for an industry, or two, etc...... off of the 'old main' to the RR Museum/old station, now a stubb ended siding, due to the 'line relocation, a while back.....
Just a few thoughts, hope this helps some.
Carl