I think that the hardest question that you asked was when is the right time to buy? This is a question that is really answered on a case by case basis. Based on what I have read from your post right now, I don’t think now is the right time to buy for you. Also per earlier thoughts I have posted, I think the new developments that have been built out over the past few years could be great candidates for good deals in the next few years due to people who overextended themselves.
Also per your statement you think that the 500k may be biting off a bit to much, then absolutely listen to that instinct.