I have raised eyebrows at Madison here. Hooking up with the bride's, your old school friend's, father at the wedding is a bold move and the fact that there's a well-appreciated chunk of real estate on the table makes it even more interesting to me.

--Depending on where they live, Madison may marry Dad and get the house or force its sale in the subsequent divorce.

--I don't love the suggestion of a life use arrangement for this. Isabella and Madison are agemates. This effectively disinherits Isabella and allows Madison to trash the house or whatever she likes.

--If the house was a gift from the deceased mother's side of the family, were there terms attached? It seems to me that people who give houses to a couple may do so under a trust arrangement if what they want is stability for the children of the marriage. He doesn't mention a trust, or the late wife's will, or anything.

--I would propose that Dad gift the house on to Isabella now and move out. If Madison still sticks around, great! If not, welp.

--He doesn't need grandchildren if he's planning on having a second family with Madison.