It's such a gamble.

Investing in general is gambling. 

Do you think I'm gambling by bidding on the property if the risk is no comps and the value of the property coming back too low.

Or as @Chris Grenzig mentioned, you could gamble by hiring someone off Craigslist. 

Gambled a bit on the color with it being a bit of an artsy area.

Otherwise it is like Gambling If You invest in real estate and buy REIT, it is disadvantage to you return because you are double exposed to the same risk in the same industry.  

You can start with less, but the lower you go the more you're gambling with your investment.

But I'm planning to diversify the portfolio towards $flow+ in the near future, since appreciation is just another type of gamble (calculated risk, but still).

It’s a gamble, have a back up plan.

When I book hundreds of rooms at a shot, they tend to give me the best pricing, since DUH, it's vegas, they aren't making their money off the rooms, but off the gambling, the liquor, etc. and Im putting several hundred corporate people in their property who are all going to spend money.