So I started creating an on boarding system where I have recorded videos and documents and protocol of how to run business.

When faced with scenarios like this, it's tough to answer such a specific question with limited information. 

One of the most important steps you can take as either a startup landlord or seasoned one is to use a platform specific to property management as it will elevate your operation and save you tons of time.The good news is that nearly every software designed for landlords includes these features.

My question is around property insurance and specifically what are everyones MUST HAVE COVERAGES. 

While it may not offer as much diversification, at least with a syndication, you can review the specific merits of that particular deal.Also, the fund operator typically has different motivations than the syndicator.

Most PMs, especially the well established ones, will not always flex for specific clients like this but it could be an option.hope this helps.

In many cases bigger banks or lenders have specific programs that cater to first time home buyers and investors. 

Are there specific market indicators or property traits I should be paying attention to?

You didn’t mention the property or deal specifics, but for many deals in the recent years, there have been amazing and unusual gains due to multiple unnatural circumstances.

I mentioned these specifically because the people running them have high integrity and what I would caution people on is all the new debt funds popping up that are being used to fund their other ventures that are in trouble.