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The way the US tax and rental lawas are structured buying is always better than renting
Generally agree with you. The mortgage interest deduction favors buying (assuming you're itemizing). I think where many get it wrong, though, is on flexibility, Every time you move you're losing 5-6% on realtor fees, so if you don't plan on being somewhere for 5+ years, you're likely better off renting.
Not sure there's ever a perfect time. Either interest rates are high and demand is low, or interest rates are low and demand is high.