So Towns...
I don't have any drawing software and that's probably a good thing: my art is terrible. Use your imagination please.
First off, I propose the town's name be something like "Golurkmoar Town" or something insinuating you aren't very good.
The first house would obviously be our player's house. Same basic layout, but let's avoid the stereotypical "I don't have a father bullshit". There are two routes to take here imo: Chaos is all smogonite's father and should come into play later (of course chaos will) or the father is actually there...
The town layout should have a small river run through the middle and a few bridges going over. In general, there would be four structures. Your house, the rival's, the Luck-Sack leader, and a small shanty-turned lab. If you hadn't gone to the lucksack house first, the shanty house would have nothing in it. Maybe one or two trees, a few blocks of sand at one part by the river, some aesthetically pleasing stuff.
If the father IS in the house, he should be raving about what a good child you are, not involving yourself with adventuring and aiming for a good degree. As the adventure goes on, his opinion could become progressively worse. The mother shouldn't exist imo to model "No such thing as a real girl/woman on the internet".
There should be two other houses, probably one of the rival and perhaps one of the Luck-Sack's leader. Standard rival house, but mother constantly nags the rival to do homework. Rival claims it's all done but when you go upstairs, you'd just see a huge video game setup and no desk in sight. He'd talk briefly about how he's a master LoL player and then suddenly rage because he just got crushed. He'll decide to go train pokemon due to his ragequit.
Assuming Luck-Sack's leader is Verlisify, there needs to be a Rare Bone in his house and this can be the start to the player's economy. Inside the house, regardless of the leader, there should be a bunch of pokemon cushions and basically anything that can represent more interested in the "friendship" side of a stat-based game. There would also be a glorified alter (seriously, with stain glass windows or something) with a TM for Swagger. When the player tries to grab it, it would trigger the professor to come in and start to teach/lecture the trainer about the disasters of swagger. Eventually, this would lead to standard "Pick first pokemon, ADVENTURE" attitude. More importantly, the professor would make some comments about how he could get arrested for breaking and entering. If it was Lonelyness, comment to be made how it wouldn't be his first.
The Lab would actually be a small shanty house. "Budget cuts were made...". However, there will still be an area for options. Later on in the game, the proffessor can reveal the shanty house is actually just a coverup and that his REAL lab is in the basement. It'd look like something straight out of Tron or something with a big red button that if you push, you'd blow something up... Preferably a Luck-Sack base. With the justification of "No one actually leaves a base after getting beat by a child... we'll just use explosives!". After leaving, adventure as usual.
Standard "technology is incredible" guy. Few other NPCs that should make note of how good they are at pokemon with their swagger teams. Fro the hell of it, let's get an NPC that just yells "LEEEEEEROOOOY JEEENKINS" (of course longer and far more annoying) whenever you talk to him.
/end town theory.
We do need to figure out who the professor is to poke fun at them a bit. Since the Firebot guys are such good teachers, I propose we use a recognized shitposter from them (RODAN/TiK) because why actually do it properly and use a regular mentor?