The really dark part of this story is I put the property on the market for about $500,000 and did not get one offer for about 5 years.

Only problem is I got to know about the really bad neighborhoods in the Ferguson area from a local insurance agent and am getting second thoughts if I should even go with this. 

Since you’re only in Bend you should really try to come to town and see for yourself how brutal the competition is.

First thing I would do is educate yourself as much as possible by reading some good books or watching some youtube videos.Second thing I would do is is hone in a bit better on what type of investment you'd like to do. 

Great point on accounting for a property manager, I will definitely find out what the going rate for that in my area is!

The deal is I am buying my parents house with mother in law suite to live in and rent out the 1300 sq ft mother in law suite.

It appears that the high sale prices are not stopping people or investors from buying, so my question is, is it wise to buy a property at an inflated price which in turn makes it harder for the numbers to work, or save my money for when the market turns, and properties are being sold at a reasonable price?

So my question is, is it ever worth buying high?

Which means Selling high is is great for you. 

do so.Lastly, as hot as this market is I would be surprised if several other investors are not looking at this same property and planning to start a bidding frenzy.