Steve,
A few years ago I had my eyes on a 1999 SL500 Mercedes. It had to be Smoke Silver (gold color) to match my wifes car but I could not find one up here with low miles and for less than $40k which is like less than half the original price tag. I found one down in San Jose for $20k so my wife a bought two round trip full price Alaska Airline tickets thinking that if we didn't like what we saw then we just use the other half of the ticket to come home later that day after having dinner and a day of doing nothing. I could get a refund for the other half if I bought the car.
Long story short. I bought the car next to the one that I was looking at for a bit more but it was perfect and we enjoyed two days in Napa Valley wine country getting buzzed by those little shot glasses of wine at many different wineries. What a wonderful trip and we only had to drive one way to see it all.
My next car will definately be purchased somewhere I have not been and do the exact same thing. I never buy new so it is a bit more challengeing to find the right vehicle.
I wonder what the math would be like if you could figure out a trailer and truck and COE if you sold the trailer and truck when you got back. I am very tempted to buy a newer Boston Whaler down in Florida someday and trailer it back home. The discount on those boats down there is almost worth the gas. I have a few clients down there that would gladly store the boat till I got down there. The trip would probably include disney world and stopping buy a few of the other guys on this forum that had simular trucks. I could even stop buy and see Spanky's COE's.
I have never made money on anything that moves on 4 wheels so I would only calculate how much I am willing to burn to have a good time.
When I owned and maintained airplanes that was the biggest black hole I have ever come across. My COE is just a big time vacuum.
I used to fly demo planes back to the Osh Kosh airshow for a local kit plane company and then sometimes drive their big moving truck back. We did these trips in 9 hours flying and 32 hours driving. We would draw straws to see who would fly and who would drive. I lost only once. The best two week vacations I ever had till the kit plane company changed owners and they decided to have their own employees fly the planes.
I still a a young kid at heart when it comes to roughing it and going for hunt.
