My ultimate goal is to generate $11K per month in passive income and I believe I can do that by purchasing 3 more single family homes in my area and paying off the entire portfolio.

Do nothing: The Trust ultimately owns the LLC and therefore even if the property is re-deeded to the LLC, trust has ownership right too3. 

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Its going to vary, ultimately the costs will be whatever a contractor is willing to do it for. 

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Let it crash and the HYSA & Tbill holders can scoop up after tapping some reserves to survive.

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Ultimately, that type of tenant is telling you they will gladly pay more if they can pay a little late. 

Many of the most successful (read as: founders that are worth well into the 9 figures, have survived multiple market cycles, etc) syndicators I know started by working in real estate for other companies.  

However, the property could be developed with several buildings and could ultimately accommodate more than 36 units.