At least in the sheriff's sales, the auctioneer is not engaged in trying to hide things from the buyer. 

I found it a challenge to find Property Managers in my area of interest with stellar online reputation. 

The challenge is that that. realtor only has so many clients needing houses with owner finance.

My biggest challenge is liquidity.  

:)  I also hear of a lot of challenges getting mortgages as a Canadian Citizen, Setting up your corporations right, the exchange rate keeps you on your toes, and the unknown of what a downturn in the market looks like are enough to make us research a little harder before we just jump down there. 

They say, "the roads that lead to places worth going, are full of challenges and disappointments."

Cozy interface is challenging to me and not very intuitive IMO.

However, there are challenges ahead.

But...If I wanted to engage in other REI deals with money straight from my savings account, would I have to form a separate business entity in order to take part?

Not to make this even more challenging for you, but if you get an inspection make sure it is from someone who has a very good reputation for being thorough.