I don’t understand the “long run” rational. Housing goes in cycles and the average bottom to top difference is 30% of the home price. So if you entered (bought first home) at a cyclical top as opposed to a cyclical bottom, then you lost equivalent to 30% of that home’s price. No matter how long you live in it you have missed on that much money. If you buy now and your friend buys 3-5 years later at bottom, then it doesn’t mean tht in 30 years both will have same bottom line. Just for being prudent and patient, your friend will have that +30% more than you for now and after 30 years too.

Also, the current rent equivalent (cash flow) value of a UTC condo to give decent return (6%) on your downpayment is around 180K (using average 1BR rent of 1250 in UTC and average HOA of 250, 6.5% interest rate and ofcourse zero appreciation in future 3-5 years).