If the resident has issues with the quality of the housing such as a failing roof or HVAC issue we would advocate strongly on their behalf as well.

It's time to get it back.Any time I need something from a tenant, I set a deadline for their response and a consequence/penalty if they fail to comply.

Keep in mind that banks were failing all over the place at the time.

You need to set them up to expect failure.I am not saying you will fail, but there is a lot that can go wrong and ruin their reputation.

Several times we hired a professor/soil scientist who taught most of the soil scientist in the state.The township/SEO (Sewage Enforcement Officer) has historic records and can tell you if a specific lot is:A. passed septic testB. failed septic testC. never testedI used to be a licensed SEO and took all the state courses to do perk tests, so am very familiar with the process.In Bigger Pockets Podcast #82 we only slightly touched on land subdivision, development and vacant lots.

Do I put a low deductible on my wind/hail and then use insurance to pay for a new roof once it fails? 

Most newer investors will input the numbers to the best of their ability but fail to consider how each input has varying levels of effect on the final return numbers.Experienced investors develop a deep sense of sensitivity and may not even need a model for them to know where the greatest risk points in the project are.

Hypothetically, if you tumbled down and started failing, would they be there for you? 

Make calls, fail a 1000x, until you carve your own path. 

I tried networking in a few local groups on Facebook but I don't know these people well and their recommendations have been a part of my failed search so far.