Sometimes it's ambiguous, but even then, why should I bother with the company that has numerous unresolved lawsuits, versus another company that is virtually the same but has none.

To process a new owner payment the system takes an extra week or two.

Since there are often different entities, there are different skills and systems needed.With that said, I can tell you are definitely better at building systems that I am (I have built up some best practices, but they mostly reside in my head).

Not every older system needs to be simply replaced.

Cross border taxation is very complicated, most developed countries like the US and Canada have sophisticated systems to ensure their residents pay taxes, and you are not likely to be able to achieve your goal of not paying Canadian taxes on Florida income while a Canadian resident. 

City assumed it was tied into new sewer system. 

For older properties, expect a higher CapEx due to potential issues with major systems like roofing or plumbing.

Are the comps, really comps (i.e. ranch vs two story, sidewalks versus no sidewalks, subdivision vs not)?

However, its downfall (and really what makes it so easy) is that it is a single-entry system. 

Use the net cash flow from those buildings to them buy your "house" and just let the system churn.