And you gamble sending them mailers.

There may come a time when you will need property management or an unexpected cost comes up and you will not have the buffer to cover it.I would agree with Daniel, and advice you especially for the first deal to not gamble on appreciation but to buy a deal that pays for itself over the long run.

I have heard of people getting sucked into drugs or gambling and destroying a successful business.

You're already making a great profit, I would gamble and take the percentage instead of the $20k.

So you are taking pretty big gamble with this.

So you choose to gamble on losing $2k by "chancing it" as opposed to spending $200 times 10 homes or so?

In a couple years it may pan out so I'd say its a bit of a gamble, I don't think the area will deteriorate/depreciate so you're safe in that regard.

Yep, I'm aware it's a gamble (as a bead of sweat drips down my forehead) but I do have some reserves, I'm still doing a little consulting for my old company, and I have a very supportive gf (who btw is from Chicago).

I just want to be able to trade spot gold and contracts for difference without and offshore brokerage.

Real estate is gambling.