I'm not thrilled with the way it looks with the oak as the oak looks orange.

This in itself should bring the value of the property from $5,600,000 to $7,200,000 (and this is considering a more conservative exit cap rate of 100 bp above the enter one), so at the end of the day the increased value would make the investment IRR in the 15-20%.I have a considerable amount of my portfolio in the stock market and believe me, no 2.5% dividend yield stock is going to deliver that performance over the next few years, especially considering the current inflated P/E ratios in the market, unless we gamble on ridiculous appreciation, so I fail to see how your comparison is fair.

Home warranties are basically gambling that you will at some point you will collect on it and hopefully it will cover the repairs without costing you too much.

The other challenge/issue would be the other current long term tenants that reside at these multi family properties during the "test" phase as I am sure they wouldn't be thrilled with new neighbors daily but I suppose that's a separate issue.

I did give some thought to the whole PMI portion and wasn't thrilled with the idea (who would be though).

I think taking the risk and riding the AirBnB wave it's hot is probably worth the gamble..

The last house I bought had a clay sewage line, I would have been thrilled with cast iron. 

I’m especially curious because a few rentals were picked up by investors in my area at well over 25% above last year’s comps and I can’t help but wonder if they’re gambling on near term rent increases....or if they’ve just overlevered their way into non performing assets because of fomo.  

Yes you still need insurance but that is your only form of protection you are gambling.

Knowledge is power, speculation is gambling!!