The gamble is whether the annual loss on the rental scheme will be mostly covered when I eventually sell the condo.  

What do they care if I buy poorly and lose my shirt down the road.Again, just following what the market and others are doing sounds like gambling , not investing.

I took gamble needing to get  the rent coming in and almost 4 years later they have been the best tenant.

On top of that you should know exactly who is going to buy or rent it from you and all the terms of the deal.Real estate investment is not gambling.  

But I have read and feel that that is almost like gambling.

If not, are you just looking to gamble?

I thought this was a fraudulent charge since there was no record anywhere (and still isn’t nor can quickbooks provide a record / receipt) so I called my bank to dispute the charge.

It involves a legal battle, a fraudulent contractor and much more.  

I used to live near Pasadena and absolutely LOVE the charm of all those historical craftsman homes, especially the Gamble House ... unfortunately, this was before I became a RE investor.

I knew I was gambling when I mentioned money but I've seen plenty of posts asking for advice and only receiving welcoming messages with no substance so I wanted to get some response, even if it was just fishing.