Too much free time on my hands

I have a friend here in Mississippi who moves around a lot. They usually spend 3-4 months in one spot before being sent on the next adventure. After years of this, they have really learned to keep just what they need and their house is remarkably clutter free.

Their living room consists of a couch, chair, end table and tv. Dining room is a table, 4 chairs and a small book case to hold their daughter's school books. Their bedroom is a bed and 1 dresser, while their daughter's bedroom is a bed, small table and chair set, doll house and toys. All of her clothes are kept on shelves in the walk in closet. While some people would see it as too stark, it gives me a sense of tranquility be be surrounded by so much open space.

I come from a long line of pack rats - on both sides. My grandparents were hoarders. Yes, like the ones you see on the evening news, except for piles and piles of cat food cans they had furniture. They "inherited" the entire households of their parents and as a result ended up with for example, four complete dining sets (table, 30+ chairs, buffet, hutch). All of it saved because it was "worth something " and apparently one day they were going to cash in on all of it. Of course, after being piled around the house and neglected for so long, it wasn't worth anything (if it ever was) and what wasn't thrown away is currently all sitting in my aunt's garage.

Don't get me wrong. They had their share of junk, too. Their basement was full of boxes of things like Better Homes and Garden's magazines from the 1950s and clothing older than me. All of it kept to satisfy some deep need, I suppose.

So the dilemma I am currently facing is that I have some things that I don't necessarily like, but I keep out of a sense of obligation. For example, I have a GIANT hutch that is currently holding our school stuff. It is huge, dark and over powers the room. I had thought about painting it white but after thinking about it, I am not sure. Do I like it? Sure. Do I love it? I'm not sure. Would I love it more if it were white? Maybe. Enough to drag it from state to state with us is the question.

So my question for everyone is - have you decluttered something and later regretted it?