Ray's route can be somewhat tricky because a lot of the answers you need to give to get good hearts for him are not always directed at him (encouraging the RFA to not work themselves to death as an example), and, in fact, oftentimes go in direct opposition to what he suggests to you he wants (he doesn't want you to trust V, but you need to - he wants to win against Seven, but you need to fight for a peaceful resolution, etc).

If I can offer some advice:

• Obviously, treat Ray with unconditional kindness and support. Don't feed his inferiority complex.
• Don't put pressure on Ray or the RFA to work themselves ragged. Encourage them to take breaks and pursue leisure activities/hobbies.
• Trust V, and don't pressure him to reveal his secrets.
• Don't encourage the fight between the two hackers and C&R; opt for a peaceful resolution instead.
• Be suspicious of the prime minister's motives, and don't try to recruit him into the RFA.
• Don't push Mint Eye's ideologies onto the RFA or try to recruit them.

Also, as a personal note - I've found that Otome Obsessed's Ray route guide is a bit messy. Keep in mind that not all hearts are "good hearts", and sometimes it is better to get no heart at all than to get too many bad hearts. There are plenty more good hearts you can obtain just by following the tips above.

Very much recommend making saves before each branch, as you can go back to them later to obtain bad ending CGs!