Some of these things are not hard to fix, but if you don't fix them before you get the city guy in there, the city guy may be inclined to take a much harder look at *everything*.As you said, some things will be harder to tell. 

My wife believes that this guy wants to put the home back on the market to get a higher price, and I'm more inclined to believe the seller's story that he simply changed his mind (simply because he seemed sentimental about the place).  

My natural inclination would be to pull the money out now and pay the penalty and taxes and then use that money for down payments and never pay taxes again on the cash flows. 

These companies serve some of the largest individual investors in the front range so I'm inclined to agree.

Another thought I had, but am less inclined towards, is stockpiling cash for a shift to be able to capitalize on more opportunities if there is a shift.

What it does though, in my mind at least, is create a seperation that people would be inclined to step "over" and hopefully not trip.

I'm inclined to lean that direction unless you're dealing with way more than 4 properties.Ultimately, it's down to your own level of risk tolerance and comfort level.If you do decide you need an LLC, my research has led me to believe that Wyoming is a pretty clear winner in terms of cost, simplicity, reporting requirements, investor friendliness and state laws.

I’m not inclined to foam inject my walls though for one issue in ten years.

Though things are changing, Canadians have been less inclined to sell their properties on their own or though channels other than an agent.There are folks here who have been successful in wholesaling (@William Johnson) and some who use it opportunistically within an arsenal of other practices (@Luc Boiron).  

In one sense consumers were conditioned that there must be a drop, a sizable drop, because there was a sizable incline.