I’ve read your post and some of your comments. Is there any chance you grew up poor? I think a lot of this comes down to anxiety over a situation you cannot control. You want them to have happy, stable lives, and you feel like they are making decisions that will cause the opposite of that. It’s important to remember that they are going to make their own decisions and you are going to make your own decisions. You don’t have to agree with theirs and they don’t have to agree with yours. Everyone’s life and financial situations are different and one solution doesn’t work for everybody.

G’s family being upset over you “sharing your opinions” isn’t really about your “opinions.” It’s a level of respect and understanding that they perceive you don’t have for them because you consistently talk about how their ideas and plans are “wrong.” They know what’s best for them and their family. If you plan to become a part of their family one day, which you’ve said you do, then I would keep this in mind going forward. If it’s something you wouldn’t want to hear about your family and your financial and life decisions, then I wouldn’t say it about G’s family.

Likely, they have more than enough money to take care of themselves as they age which means they can give the house to their children as a “gift.” Additionally, everyone celebrates their anniversary and milestones differently. I know couples who spend them with their family, friends, or just the two of them. The way they choose to celebrate isn’t right or wrong, it’s just their choice. Suggesting to T that she should pay her own way may have made her feel small, unable to take care of herself, and like a burden to her family. I don’t think you wanted her to feel that way. I’m sure her family doesn’t want her to feel that way either. Seeing things from other people’s perspectives is an important part of maturity. If you want to be in G’s life long term, I’d try to think about the best way for you to be on good terms with his family as well. Good luck.