If you NEED the acre lot with the snow mobile and jet ski and motorcycle in the three car garage then Podunk is your place. 

While I like building a legacy for my kids and Grandkids  . the Fact is we live in the Jet age and for a fairly modest amount of money we can have experiences only the very rich had as little as 75 years or so ago..   

@Shawn Ackerman   here is what you need to run from NY to Milwaukee  http://cirrusaircraft.com/aircraft/vision-jet/ I had a deposit on one.. but I got to old to fly it..

Even fresh paint doesn't "un-date" textured walls and ceilings.

I'd love to know how many people running this racket instead slip up and DON'T pay the HELOC, and instead go to Cabo or buy a Jet ski and then have to deal with double interest.