We bought our first house when we were 19 years old for $25,000.  We were earning $7/hour between the two of us, but managed to pay it off within 2 years.  It was a little 900 sq ft A-frame with a finished walk-out basement. We lived in the basement as the upstairs was never finished.  It sounds depressing, but it was actually pretty nice.  We moved in as soon as we got married and lived in the basement for about 4 years.  We then realized we were going to have to replace the roof.  When an A-frame needs a new roof, you might as well forget about it.  So, we hooked a chain to the house and the other end to my dad's truck and brought the house down.  After that, my dad and Henry built a new house on top of the old basement.
Our first  house before
We lived there for about  a year and 1/2.  We then sold the house and moved into my parents finished, walk-out basement (sound familiar?).  We immediately started building on 2 1/2 acres of land that we had bought a few years previously.  Henry had built several houses and decided to build our house himself (with help from his friend, John).  We started in September of 2000 and finished in June of 2001.
My contribution to the house was staining all the wood- doors, trim, fireplace, whatever (thankfully, the floors came pre-stained), and laying the ceramic tile in the bathrooms. 

We sold this house in 2004 and bought 2 more. We have also started building another one!
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Heather and Henry's House History
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Our first  house during
Our first  house after
Before picture of the house we're currently living in while we build another one. 
Houses page 2
This is what it looks like now.  We're still not done with the outside, but the inside was already nice.  It just needs new carpet.