This stuff doesn't have to be complicated.

They do not do it because they wake up in the morning and think, "gee, today I am going to invest somewhere else".This story is in fact quite complicated.

AS you illustrate with your ( what I would call ) complicated debt instrument plays.

dont over think this its not that complicated. important issues are.1. cost of capital2. knowing what a deal is or is not.3. good reno crew or contractor  4. good agent that will tell you straight what its worth when done and what level you should rehab to.5. a market that is actually moving napkin math works  trying to drill down to decimal points does not.

As for NY which is from what I see a very complicated state compared to Trustee sale states the thing to do and the ONLY thing to do..

After a long and complicated history with the current tenant, I’m now starting the eviction process.

The Title Holding Trust or Land Trust will keep your name of the public record, but it can also complicate the property ownership and management. 

I would love any advice on landlords' favorite brands or models that last well and are not complicated.

This will allow you separate business income and expenses from personal income and expenses.Since you plan to house hack your bookkeeping and tax return preparation will be more complicated because a percentage of your home expenses will be personal deductions and some will be business deductions.

So in order to really compare apples to apples it is more complicated than just the commission portion of the transaction costs.