What I've observed is owner/operators get way too attached to a property and thus overcomplicate the business of running a STR.

Good observation. 

I have heard that exploring the area in person is one of the most effective strategies, physically observing the area and looking out for rental signs and what not.

I'm far from an expert in real estate but my observation is that the real estate industry is being disrupted and new business models are emerging.

Also I think it is helpful if you can go an observe a planning and zoning meeting or two or three where these plans are presented. 

From my trips around the city I have the same observations.

If you have no prior experience, it may be beneficial for you to start as a passive syndication investor to observe how the overall process goes.

One common mistake I have observed is funding future renovations solely based on asset cashflows or spending money that is yet to be acquired.

It may surprise you that in 1995 psychologists conducted a study and observed that the bronze medalists were significantly happier than the silver medalists.

"But my question is, can a tenant be held responsible for the damage as they didn’t tell the landlord of the issue which has ended up being much more damaging and expensive than it could have been if they had let someone know"The answer is YES.... but you have to be able to prove that their lack of notification resulted in the damage..... and the damage was readily visible and could be observed by the tenant- Not always easy to do.