However, all properties in the funds are stable and we still feel pretty confident that things will pan out well.Our biggest gamble in all of our investing was with Goodegg.

I talk to a lot of California investors and it's a huge gamble to buy out of state especially a market you don't know well.

Arguably his as he gambled. 

But I also feel like it is one of many things that could be a problem or could not be a problem that unless you are willing to pay to get it checked out ahead of time is going to be a gamble.

If you're OK with a gamble for higher % gains, that's what we have done with a big chunk of our cash.

They have money and they gamble.  

You’ll develop an instinct for what a “good deal” looks like in your area, and your learning curve will be smoother because you’re immersed in the local dynamics.

Quote from @Will Riley Moseley: I've spent the past few years immersing myself in books and podcasts, learning as much as I can about the industry.

How much money, realistically, can i expect to gamble with in the beginning?  

Or as I like to call it, your selling a ticket to gamble to some gambler.