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Should we remodel or rebuild?

We have an early 1970's split level home in Vermont. 2500 sq.ft., original windows, 2x4 construction/insulation. 4 bedrooms (small), two baths (small), small closets. The house is fine for OUR family, but is definitely not what most people look for in a house plan these days (i.e. no master bedroom/bath, not a lot of storage closets, etc.) We are talking to an architect and builders about doing a lot of work on the house. The list includes, adding an envelope of insulation around the house, new windows, new interior doors, new kitchen, 2 new baths, some new some refinishing of floors, adding some decks, a screened-in porch, and landscaping after all is done.
The high/rough estimate is for $330,000. This builder has a history of excellent work and typically comes in, at or below estimated costs. The house and property (6.3 acres) is assessed for property taxes at $300,000. We love the property and plan on spending the rest of our lives here (hopefully 30+ years).
Our question is, does it make sense to spend that much money on remodeling a house that ultimately will not have all the amenities that people look for in a home, NOW (let alone 30 years from now) or should we look at minimal upgrades now and possibly razing and rebuilding with an updated home design in the future?
I know there are a lot of variables to this question, but we're just not sure of what the best approach should be. I keep thinking of the TOH people looking at our house. Would they say "Sure do this and this, and it will be great!" or would they say "if money's no object, just knock it down and start over!
Thanks in advance for any input that anyone may have!

Re: Should we remodel or rebuild?

Hi. Consider the size of the house and your age in 30 yrs. Will you really want the upkeep chores? Just a thought. May be better to not look that far down the road and do to the house what will make you happy now.

Re: Should we remodel or rebuild?

typically when the price of a total renovation starts getting up that high for a house i lean more towards having the customer go for the rebuild.
last month i finished working on a house that fits yours to a T, we priced the job both ways, both as a complete reno and as a rebuild, the homeowner went with the rebuild as the price was close to $100,000 less for the rebuild and thats not including what issues we may have run into along the way and extras

Re: Should we remodel or rebuild?

Well, for me it's better to rebuild than to repair. It can cost you more by repairing, like labor salary aspect. And repairing takes more time.

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