We put our property in Land Trusts. 

Trust your gut on this decision, often times it will be correct.  

Any advice on how I should approach people and present myself with a sense of trust?

Of course price is important to us and our property owners, but we need to trust the company will be professional, has all the proper insurance, etc. and can prioritize work as required. 

If there was a trust established, sometimes there is a decision maker for the estate.

How much time will I need to rent out the property for in order to show the mortgage company I’m trust worthy enough for another mortgage? 

They have a library of info on different subjects, specialized info on specific items like structuring entities, trusts, asset protection, tax, etc.

After a while you won't even need a tracker or a spreadsheet to be able to identify whether it's a good or bad deal just from scrolling through the Zillow/Realtor stats.More importantly, find and get to know an agent in the area you want to invest, and make it clear to them that you plan to purchase multiple houses and want to develop a long-term trusting relationship with them.

Also - what is your strategy for getting the bank to know and trust you? 

One simple example of why not to trust the FDA.I am not for more burdensome regulations on landlords and believe landlords should have more freedom in whom they rent too.