Kinda makes me think that maybe, just maybe, each asset class has their own unique pros and cons and there isn't a one size fits all 'best way to invest'...

Once you have this document you will be uniquely in a position to have something to sell.

Depending on your strategy sites like those may be fine for some strategies, but for qualified leads you need better data or you'll spend much of your time running in circles.Also, even with the better data, it can be challenge reaching some distressed owners for  a litany of reasons.  

What the cost associated with contesting would be and if it is worth challenging the city of the new value. 

He seems a little desperate and kinda bugging me with over friendliness which I imagine is because of his physical challenges, I'm guessing but he seems friendly and skilled enough and we'd be working together replacing doors and refinishing/painting that formica covered composite wood stuff the boxes are made of and replacing the (horizontal) particle board.

Also, I’ve heard being a land lord in Lexington is more challenging than other cities, such as Indy or Kansas City, MO.

Ultimate challenge being coming up with a large down payment.For this example, the owner owes 100k and the property is worth 425k.

Yep he lost but he is going to be a challenge.

Additionally, the validity of the tax suit (in @Gavin Snyder's case, Linebarger) can be challenged for a time frame of 2x the right of redemption. 

I work with hundreds of real estate investors, each one unique in their strengths and weaknesses.