Quoted from too-many-pins:
My CRAZIEST deal has to have been my fairly recent trip to El Paso, Texas this past Spring to pick up some "junk machines" & parts. I drove almost 6000 miles to buy $3500 worth of parts machines and parts but that isn't actually the crazy part. What was crazy is I did the math and I figured the weight of everything was going to be about 5000 pounds (or more). At the time I made the deal I had a Kia Minivan & a 6x12 cargo trailer with a weight capacity of about 2000 pounds max. Most RATIONAL people would have just passed on that deal but not Skip.
What does Skip do - talks his wife into buying a new 3/4 ton Chevy van to make the trip. So after spending over $28,000 on the new van, almost $1000 in fuel, and another $700 (or more) for motel rooms I picked up the parts that had a retail value of maybe $10,000 on a great day. Basically driving almost 6000 miles just to break even at best once everything was considered.
Now for the SAD part of the trip. While I was in El Paso I wrecked the new truck & my nearly new enclosed cargo trailer. The truck was 18 days old and had just under 3000 miles on it. One minute it looked great the next minute it had $13,000 worth of damage and the trailer was totaled. Thankfully I was able to drive both home but my new truck wasn't new anymore. Worse yet is I changed insurance companies when I bought the new truck and I had to explain to them I just cost them over $16,000 after having their insurance less than 3 weeks.
In the end my insurance rates only went up about $130 a year & my deductible was $500 on each the trailer & the van so my mishap didn't cost me all that much but my wife wasn't very happy about that trip.
Most of your stories hit pretty close to home. Very much enjoying them.