I wouldn't call it a self-insert thing. This is the only reality I know. Love doesn't exist between two people who don't know completely about each other. If anything does, it's infatuation. Sorry if it seems like self-insert, but I am trying to be a bit on the reality side. And even if it's a self-insert, it will perhaps teach people the lesson I have learned in the past few days. Terrence will grow to know what true love is, that's what the story is about. That part is something I can't or won't pursue.
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Burgh, who heard about Terry's acts in Pinwheel Forest, asks him if he wants to be a Bug Pokemon Trainer.
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This is an excellent plot point. A very good idea you have come up with here. Honestly, it'd add a lot to his character development. Also, I'd like to remind that Burgh is an artist, so all his apprentice are more or less good artists. Artists need imagination. Guess who has an incredible imagination?
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He is met by his mother in their house and he goes back into a daily routine. His mother worries about his wellbeing, since he has looked energyless and dejected.
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I was actually counting on his mother being the major factor breaking his will to travel with Gwen, but I guess this is good too. Just a bit uncomfortable, but I am really happy with the ideas you have here.
However there's one bit, I want to add here. This fic, as you know isn't completely a trainer's fic, and it is certainly not a good idea to write this in the anime-style (not saying you are) of travelling when it is supposed to be more of a romance/drama theme. Which means, while progressing them along the journey like a regular trainer fic, you should write it in a way that each chapter ends with its own twist rather than journey from point A to point B.