I'd say Gym Leader because you also seem to be a community leader as well. I've very indecisive about my favorite types. I'd think I'd be either a Ground or Ice type gym leader but also use pokemon who can learn Ice and Ground types. Although I also would like to be an Elite 4 member who fights evil teams but it seems like you'd have to be on call a lot.
If I could have any starter I think i'd go with Togepi. I've been replaying HeartGold and Togetic is the boss. I'd still at some point get a piplup, but I'd start the journey with an Happiness evolving pokemon.
The ice cream game requires you to use strategy to get as many scoops as you can stack without it falling. The higher you go, the more points you'll get. Combee will occasionally fly at the pile, so having it properly balanced is key. I'm getting a bit better at it, but it's kinda hard
Yes, I made friends with an Oddish, a Sunkern, a Luxio, and a Mareep. Basically, you'll see a shaking bush. You click on it, the Pokèmon will pop out and want to play a mini game. If you play and get a score, the Pokèmon will be happy. Once you take 10 steps, you'll reach the Dream Tree. If you place a berry at the base and "make a wish", you can choose which one you want to meet in your actual game. Once you wake your Pokèmon back up, you can connect to the Entranet, and go to the top of the screen to enter the forest. The Pokèmon you "wished" for will appear, and you go to a battle screen. You toss a Dream ball and instantly capture it.