It's been good so far though and are looking forward to establishing our roots here.

I have spent the last few years out of college doing data analysis and visualization in Washington DC but have returned to my roots in Martin County, Florida.

Just wanted to clear that up.Now secondly, as to the root of your question, whether or not to 1099 the tenants for this past due rent they owe. 

For example: was it caused by poor grading/drainage, tree roots, post-tension cable failure, water leak, poor moisture management (i.e. no sprinkler)? 

I personally invest in Austin (16 units currently, mostly duplexes and fourplexes), but maybe more to the root of what you're really asking; there's a TON of interest from California investors in our state.

Rooting for you @Brian Schroeder

Even if attempting to clear a french drain doesn't work...and it might not given it could be compressed or damaged by roots...

I think a lot of people have got to the root of your question.

Tree roots can damage any plumbing as well as the foundation.Roofs - in my market, they last 15 years and you need 5 years of roof life remaining to get insurance.

Lots of tech companies have planted roots here the last 10 years and there has been a large influx of good jobs.