Point the exit door out hinting they should start looking...…  They are trying to be disruptive using it as an excuse.

What are your helpful hints?

Your statement about the money guy is doing well enough hints at a level of casualness about his money, so please remember how unique his money is to you.

Hint: none of them.

Not really an emotional issue, which your last sentence hints at, as much as it is an economic issue.

(hint, see profile)

As @Jay Hinrichs hints at properties at that price point, are likely to go south and will take a lot of maintenance repairs.  

But I keep an eye on them anyway, from the point of being for sale, to being sold, to I will drive the neighborhood and see if they are being remodeled, to the flip price after the remodel.Doing this serves me thusly:I get better at recognizing deals, especially in neighborhoods with which I'm less familiar, or are/were/getting sketchy;It allows me to reexamine my own concept of "the deal", such that I will have greater success in my offers and ultimate purchases;It provides hints about upcoming economic situations - overheated prices, oversaturated rental markets, etc.When I see a house I was watching sell for 10-20%, or more, higher or lower than what I thought it should be valued at, I am forced to review my own criteria - are my assumptions about the market correct?

Also , any advice tips / hints for managing remotely would be appreciated as well .

HINT:  Find an investor friendly Realtor.