The 8 property portfolio deal may be an all-in gamble considering I have no experience in owning out of state properties.

Even if the home is going to cash flow 2% a month, I feel like its a huge gamble. 

Appreciation is speculation a form of legal gambling.  

Naperville is a good place to buy and hold for appreciation but personally I think of that strategy as gambling.

But buying at retail value simply based on the hope that values will continue to rise is like gambling.

The point is, it's a gamble.

I owned a bar with an apartment in the Dominican Republic when I went to college and It was so frustrating to be so far away and have to rely on local boots on the ground to relay data (in fact the manager spent all my cash for the project on a gambling Christmas cocaine party, ended up in jail and my boat got stolen by some Haitians trying to migrate to Florida but thats a whole different story).

The deal was up 70% in 2 years which was a great 35% ROI a year but I think the GP wanted to gamble and go for the 120% in four years which people can argue if it was the right choice in this sellers market.

Unless you know exactly when the next dip in the market will be you could be attempting to gamble on that and lose if nothing happens for awhile.

Looking forward to equity is one thing, but anticipating appreciation is tantamount to gambling.