You made a decision given your life circumstances and you have to be ok with that. Regrets that can't be change is just torturing yourself.

I use a "Debt Dash" approach to paying off debt. I recommend people focus on paying off the debt with the lowest balance first. So if the primary has less debt you would focus on that.

We have to protect ourselves by doing our own homework.

If you'll have enough saved and nobody has to take on debt and you want to retire, shoot go for it.

When you give people who are being financially responsible money, you are enabling them to continue a bad habit. So you are actually helping by saying, "Love you but no."

I think you can save and spend to live for however long you live. You just have to be flexible if things don't go as plan.

My rule is when in doubt hire a professional. You could do it just this year and then you have direction to resume doing it yourself after the consultation. What you don't want is to do it wrong and be hit by a huge tax bill. Remember the old saying, "Don't be pennywise and pound foolish."