Thank you. I agree with everything you said, and I would hope at this point I have learned my lessons about debt!First, I am so excited that you are getting BIL's house moved along and retiring the debt and all that comes with the debt. For me debt is so stressful-- getting rid of that stress is something to celebrate!
I totally get the crying thing, from both sides, I think. We confuse money with the ability to do things for our families, for ourselves; money is potential and as we get older, we worry about dwindling potential and we worry about legacy. It hurts to NOT be able to leave a legacy--but I think that then we get confused and use the money available to us for the wrong things--fail to take care of ourselves, fail to realize just how much it costs to live. The BIL house seems representative of that confusion, that vagueness--it is not okay that it was maintained by the debt that you took on--it was living beyond means, if that makes sense. So you were trying to be kind, to save everyone--but it ends up hurting you with the debt.
I heard a good saying about debt yesterday--that we keep getting situations that tempt us to solve them with debt until we learn the lesson, but that the opportunities to learn the lesson get increasingly painful. So if that is true, then maintaining the house debt to buy a vacation house would be yet another in the escalating lessons--if you had not learned the lesson from the last time you bailed out the house, if that makes sense.
Anyway, I kind of understand both angles on this crying question, I think. We feel the pain and then we grab at our addictive substance of choice to deal with the pain--for some it is booze, for others debt. Better to do what you are doing, and separate out the real issues from the debt response.
SO glad you are going to be out of debt by end of year. What a Christmas present that will be!!
And then save up and pay cash for the vacation house--it will happen!