Makoto's entire Confidant story is about how she sets herself up for it without thinking too much about it though. I think it counts.
What I would like though, is the removal of this silly "answer the big question" flag at the end of the route, but rather make choices throughout the entire route count. Replies during events should contribute both to link points as well as romance points, and if you gather enough by the end it should allow you to get together, otherwise it should just seamlessly branch into a friendship route.
Buy all the DLC. IMO if you are willing to invest time to play the game again, you should be willing to invest money to essentially buy the game again. Open your heart, and open your wallet.
/Atlus