You're not going to do it. You didn't do it when the market looked a lot better than it does now (and you missed out on gains). You're so afraid of getting it wrong and appearing stupid to both yourself and all the people you've talked to about the market since you sold that you won't take the risk. Alex
You're right - I won't do it probably for those reasons.
I'm going to go heavier into internationally diversified stocks, take on some debt to do it, and re-evaluate the property in 12 months. That gets me the tax shield I'm looking for in the short term.
I have softened my stance a bit though - I won't necessarilly try and pick the very bottom - when it looks somewhat reasonable by historical standards I will buy in, and once I am in I am going to leave it alone and not be so obsessed by opportunity cost.