I gambled on the water restricting supply.

It is gambling.

It is not to say section 8 is bad, it is just to big of a gamble for our system We have a very strict screening and placement policy, obviously all within the equal housing parameters.  

But predicting what part of the city will transition from high crime with large levels of abandoned houses to a great area to live is more of a gambling game.  

I don't know enough about this, and it sounds like a gamble to me.Use equity in my existing home to invest in a rental property (but this sounds like a scheme where I would take a HELOC for a down payment on an investment, to be able to take out MORE debt, meaning I have to rent or sell the investment property for even MORE money to cover increased debt costs).So, are any of these options better than the others?  

It would be better that they bring the material and show you the receipts for the authenticity of the products.

Love the pointers at the end, calling out all the help you have received and the bigger pockets episode specifically.I am actually going to go back and re-read your whole post, thanks again, I very much enjoyed the authenticity and willingness to share!

I just don't know how these people are making money unless they're hoping to continue to see appreciation, which is a big gamble.

Is it a little more of a gamble?

We definitely sound very similar in our risk tolerance (and judging my your company name you may also have a background in "gambling").