While I still run their credit & background report, I'm looking to see if they have any prior rent collections / judgements, or evictions.

I believe this is true for most folks, am not interested in scrambling to find and risking my judgement on those few providers who go above and beyond, especially far from my home base. 

Hopefully they have opened up the Napali Coast trail by now after that huge 50+ inch rain storm a while back.    

I’m currently negotiating a triplex that was flooded in April from all the rain fall.

A lot of comes down to either working with people that have been referred to you and you having knowledge that someone you trust has had a positive experience with them, or doing your due diligence on the contractors portfolio, asking them for multiple references you can call and making your judgement from there.

They need to be elevated off the ground a little so prevent the bottom getting rusty from rain water. 

The Flint Hills have gotten TONS of rain in the last two summers so I would just caution you about buying anything in the low ground.  

A percentage of the judgement?  

For instance, we know roofs are critical due to the year round rain.

People could use solar for electricity, collect rain water and most of them have composting toilets.