What would you do?

We live in a quiet community where the houses range from starter bungalows to upscale mansions. There are no "bad" areas or shady streets, just families living outside the big city, raising their kids or growing old together. Our first house here we lived in for 2 years before we outgrew the size of it. A tiny bungalow with 3 bedrooms was okay when we had just 2 kids but as we grew our family, we knew we'd need more space. The house we are in now is a decent size but not huge. We've been comfortable for more than 20 years here. As the kids have gotten older and bigger, we are now starting to feel squished. We cannot fit everyone in the dining room for dinner and our living room is tight during celebrations, especially Christmas, with the big tree. Our oldest daughter has now officially become a single mom and her ex-husband is refusing to sell their house, so she's come home to live with us, bringing along our precious 2 year old grandson. Her hope and plan is to go back to school full time for 4 years. Currently, she works full time and goes to school part time.

Our mortgage is almost done and we've been saving for a number of years to either build on our acreage or buy on the coast. We never bought this house to be our "forever house" but it's been a great place to be settled for all these years. Both of us were used to moving frequently as kids - my dad was a realtor, so we were always packing up to move to the next new house he fell in love with and my dh's family rented and moved often. When we first got married, we were flipping houses and that saw us buy, renovate and sell 4 houses in 8 short years. Then we found this house, anticipated it would be another flip but here we are, still renovating and still enjoying our space.

Last week, we started to talk about buying a condo for dd and grandson. They would like to have more of their own living space and we would like some of our space back! It's not affordable to rent on her own with the current market here unless she moves to the big city but she'd likely end up in a seedy part of town. Plus our grandson is in the most amazing daycare that has a 2 year wait list. Moving to the city would mean a change from his very stable childcare to something new and likely not as good. Started to look at what a condo would cost and my heart began to race. Yes, her rent would cover the mortgage payment, property taxes, condo fees and insurance and she would pay the utilities as well. But the tax implications seemed way too complicated and it began to become a very stressful search. Then we found a house with a walk out basement that started a conversation around finding a house to suit all of us for the next 4 to 5 years. Dd has committed to paying the same rent that she would have paid had we bought a condo. Her offer, we've accepted as it will help with the additional costs we could, depending on how we do it, incur.

Hmmmmm.

Now comes the hard part, deciding if this is the right move financially and if we're ready to move forward.

Do we buy a bigger house then sell down the road, once she's done school, then move to the coast?

Do we stay here and tell her she's on her own, too bad, so sad?

Do we sell this house, build on our acreage, live on it for 6 months to get the most equity, then sell?

Do we sell everything and just move to the coast?

I love the last one!! It would mean leaving the stress here and watching sunsets over the ocean every night. The only flaw with that beautiful scenario is no jobs there for us!!

Back to square one. Decisions, decisions .... oh how I hate these types of decisions!

Question of the day: 
what would you do?