dumbest move? letting my wife choose which brokerage to manage investments and getting into a couple of managed accounts - lost 50% in a year - got most of that back, but one is supposed to be ahead, not catching up.
next dumbest move? not listening to wife when she wanted to get out of the market in July 2000 and put it all into two lake front lots on the Delaware shore. Had we done that, we'd have increased what we invested by a factor of 10 by now.
best move? after being forced to sell all the stock from 15 years in a closely held publication company -- stock that went up btw 18 and 24 % a year, rain or shine, I took the cash and built a house 3 blocks from the beach. No mortgage, low taxes, and the house is worth more than 12 times what I paid.
Not even the present mortgage crisis has caused any price drops in this beach town. Only effect of financial crisis, credit crunch, and gas prices has been a drop in and more competition for summer renters.
As we don't now and never have rented the place, who cares?
Plan to retire here at the beach for as long as it takes to make it principal residence, rent the other house until prices come back, sit on the beach, read books, take photos, travel a bit, and paint.