I think I have got enough knowledge and capital to buy my first SFH or duplex rental property, but my wife thinks buying rental properties is gambling.

That is exactly what I see, buying condos from a wholeseller seems like a real gamble.

I would make sure that the lease and any guaranty accurately reflects the deal you agree to.

It seems to be pretty accurate in my area, but I have seen some where the zestimate isn’t even close.

Flipping is all about understanding the math and accurately predicting rehab costs, estimate too low and you lose money, estimate too high and you don't bid enough to get a property under contract. 

Investors Wanted To Believe though.....I saw people pay $50k Over the HOA judgments on that gamble......a nice surprise for the homeowner who hadn’t paid his mtg for 6 years......not so good for the buyers.

I would strongly suggest... before doing ANYTHING else... to try to get the owner to allow you you walk through the property and make a more accurate assessment of the condition of the property.

Then you can get an accurate picture of the investment performance in the future once you move out.

Otherwise you will be gambling. 

For me anyone with a fico below 560 is probably a life long deadbeat, and anyone with no credit file, probably is also a dead beat, but they could have no credit for many reasons other than their lack of credit worthiness, so I assign 25 gamble points to the no credit renter and treat them as equivalent to a 585 fico.