It's very easy to fall into the perpetual cycle of "but is it good enough?"

Have you ever encountered someone from the northern regions expressing a desire to retire in a perpetually cold and overcast place where they'd spend their days shoveling snow in sub-zero temperatures?

By raising or lowering short-term interest rates, monetary policy affects the housing market, and in turn the overall economy, directly or indirectly through the effects of interest rates on 1) the user cost of capital, 2) expectations of future house-price movements, 3) housing supply, 4) standard wealth effects from house prices, 5) balance sheet, credit-channel effects on consumer spending, and 6) balance sheet, credit-channel effects on housing demand.If a bear market emerges, then we should expect home devaluation nationally of 20% to 30% or more in markets overvalued relative to wages and rents.

It's encouraging to see some small movements in the rates, but job growth also needs to soften.We're likely still in a "wait and see" phase.

If you haven't yet, look into the FIRE movement (financial independence, retire early). 

Remember, the notion of amassing wealth without investing is a dangerous myth perpetuated by self-proclaimed experts.

The greater Chicago market, while seeing movement, is still saturated with product and sales take time.

As Michael Borger said, trying to "invest" in Hawaii for a cash flowing vacation rental probably wont end well, despite it being very tempting.And again Bobs self invested bias towards this phoney perpetual appreciation speculation in the Honolulu market in silly at best.  

@Chris Skala When investing in a self-directed IRA you have a 3rd party intermediary handle the actual cash payments and movement of money between vendors, tenants and any other needs that arise.  

One negotiating tactic if you don't get price movement might be to have them bring the property up to the level of the competition.