There must be a much larger amount of people who take the gamble and fail that we don't hear about than I thought.

Lastly, everything is more expensive than you think, and as I understand it, it is more challenging to be a landlord in California.If you are betting on appreciation in the future, that might work, but it is a gamble.

You could also rent it out and eat the cost of the extra mortgage until the equity rises but at that point you are gambling.

My background is in Tech/VC and I have the networks for outsourced/ offshore software development .

You did well with the appreciation gamble. 

I could have  bought a 2 or 3 million dollar building made 100 k net a year instead of spending it .. but never have a potential 30 mil upside.. so yes speculation and gambling thats what we do.. but we also use our noggin to buy the right properties.. not just some rental house and hope for the best.

It's also the reason that investing in rentals does not make financial sense in Seattle unless gambling on appreciation.Lubbock seems to look worse every time I visit because there are few incentives to fix up older properties.

Listen to @Gino Barbaro He and his partner have consistently demonstrated they know how to buy multifamily properties at one "grade" - improve both the properties and tenants - then refinance "profitably" You should reach out to @Sarah Gamble who is also active in Ft City

However, I see more listings with price drops lately as flippers investing in suspect areas are not winning that gamble.

Of course, if you are so wealthy that shelling out cash each and every month on a property doesn't bother you then go ahead and gamble with the appreciation game but realize its nothing more than chance whether or not the property will appreciate in the short term.