WEll, I suppose I can relate. I am on my first house which I've been in for 7 years, almost to the day. We were more fortunate in that we bought when the market was slow, so the price was relatively low (130K vs market appraisal of 179K). The drawback is we bought from an absolute prick and ended up taking him to court. Twice. Winning both times. We probably should have been back more, but just got tired of the hassle and grief.
We have a pool. When we moved in, the liner was ripped. He refused to pay. Off to court.
The heater for said pool was also not functioning, that was in the above court scenario.
Come spring (we bought in winter - duh) the roof leaked. Off to court. Grr.
Lots of other crappy things with the house, so I would back your assessment of not buying a fixer upper Matt. New, while lacking some of the charm and challenge, tends to be a whole lot less expensive, at least in the short term. I need new siding, soffits, faschia. We've removed so much crap vegetation from the property. We had to finish the backyard. Which brings me to an entertaining story.
There is a raised garden in the back yard. About 10 feet by 30 feet. When we moved in, we thought we should do some work with the garden and found it to be a very, very heavy clay soil, so we got some sand and some peat to mix in. Wanting to get it mixed thoroughly, I decided to dig out a bunch of the heavy soil (the garden is about two feet deep (or raised above the surrounding ground). I started digging, got about a foot down and *CLANG* the shovel hits something hard. Clear away the dirt and it's one of those interlocking bricks. No idea why it's there, throw it on the lawn and go on digging. *CLANG* Again, another brick. *CLANG*CLANG*CLANG*
Holy crap! Some four hours later I'd pulled out almost three hundred bricks. The moron had decided to raise the garden on the basis of 0.85 per interlocking bricks.
The bright side is I had enough bricks (still have some not used) to finish paving a section in front of the garden that was just mud.
We are thinking of moving to the other side of the city. It would save me 15 minutes of driving each day. That's pretty considerable in terms of time and gas expenditure. Just all the hassle that Matt's going through, lawyer fees, realtor fees, land transfer fees, taxes. Blech. You don't get much sympathy from me Matt, but you have it on this issue.