If the property is rural and qualifies for an agriculture or wildlife exemption, then taxes will be almost nil so the cost/benefit analysis is much simpler.Buying undeveloped lots in a residential neighborhood is more speculative, in my opinion. 

I'm originally from Seattle and it's more speculative there with maybe the 0.5% rule and 4-5% cap rate.

Unless you are speculating on appreciation or intending to add value buying a negative cash flow property is not investing.

I'm not sure I like the whole idea of flipping multifamily properties as so many did with SFR which lead to speculation of enough appreciation and the lovely tidal wave (it wasn't a crash, it was silent like a thief at night) of 2008.I spent a decade in the startup space and one of the many conclusions on what makes or breaks a startup was the realization that timing before all else is the most important factor - then team.

They pile the cash flow into reserves and re-invest with the hopes of having a large maintenance reserve along the way, still a bit risky, a bit of speculation, but creative.

Three brothers owned it for a short time, as speculators.

I like "real estate speculator" with a side of educated hypothesis.

He also indicated several properties he expects to come on the market in the next six to twelve months and why: several of them where bought poorly based upon speculation in the local economy 4-5 years ago and are not being managed well; another bunch are part of a single portfolio where the owner is in his late 70s and has no heirs. 

Which one will yield a better long return is speculative. 

Again this is all speculation since I am brand new!