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Spending 20 Cheer to run improved Drills is well worth the investment.
Careful with personality when choosing player positions-- one example is the Cool Dude which boosts the rate of getting Walks if that character is currently batting, or Old Man who can't run very fast-- which means his running stat won't boost as high.
Just because you chose Live mode to view a game doesn't mean you're stuck in Live mode. You can use the menu to switch to Highlight mode at any time after the first half of the first inning (when your defense comes onto the pitch).
Speaking of starters, Tim Reeves, Dan Daley and Louis Mason's fortes will change as the player chose his/her own forte. However, as Perry Yale has the Hardworker personality and due to his above average growth, it's worth for him to be getting into drills along with the player character.
Donny Lyons, besides of having low growth on level up, is essential of placing him into drills due to his high drills growth in Batting and Slugging. He is unlocked when you reached Y2.
Defeating some of the best teams in certain regions will reward you more of reliable players when it comes to their certain skills. Crawley High (GL)'s Dwight Banks, Fastlane High (ME)'s Raul Dean, Pengate High (SW)'s Joey Walsh were reliable batters by level growth and drill growth, Spinney High (GL)'s Byron Watt for all-around effectiveness (due to multiple fortes), and Corked Canyon High (AKY)'s Julian Snyder, Mendoza High (AKY)'s Ross Lane for pitching stats.
It's worth to use the Attention Seeker skill if you have a lot of fans and if it is worth to beat the opponents. If it is not worth it, replace the skill with something else instead. Also, use the skill to those students who are weak in stats.
If you want an all-region start, start at Grand Lakes (GL). However, it is difficult to start there due to probably facing the Plains (AKY) and Mideast (ME) as the first regions to discover. If you want an easier start, take New England (NE) or Rockies (PL).
It is not recommended to start at Plains (AKY) and Mideast (ME) because you will face very hard teams in the Regional Tournament, worse, the weaker ones will be included in Local Tournaments, blocking your way from finishing the Tournament, unless you consider training your team from the Starter Teams. If you start at these regions, it is also not recommended to go on the Regional Tournaments unless you are strong enough to take these down or you have enough luck.