You need to study/read how to screen tenants and set standards.As a example a 650 credit score may be stellar for a C class property but only average for a B class.

My understanding is that the HOA is responsible for maintaining the retainer wall, but I wouldn't want to be out of luck should a snow storm or heavy rain damage break it down.My Real Estate Agent is assuring me that this isn't a problem as it's been professionally installed and the other neighbors have been living with the same retainer wall too.What has your experience been with a retainer wall?

It depends largely on how well you maintain your properties, and how many units you rent.

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It's not about you though, it's the motive and rationalization of the alleged perpetrator at that exact moment that is at issue.There's a lot to be said for cultivating and maintaining the very best tenants possible, as you would your team of contractors, agents, attorney, CPA, lenders... 

If you maintain some form of presence in Canada and, more importantly, you are planning to return here, you should be able to invest in Canada without the complicated tax scenarios.

Again, months of studying, meeting developers, property managers and getting best people on board.

I always felt that folks don't maintain and upgrade their homes around there, not just from personal experience, but even when I look at Albany-Schenectady listings today (when I want to get a sense of where the market is, we still wouldn't mind unloading our last SFH!).

I loved them so much in fact, I was 1 of 8 students selected to represent my school at the Cornell Real estate case study.

Most likely your property should be categorized for one of these.You should definitely find a competent CPA and have him or her solve the issue but I highly recommend you to study at least basics about not only depreciation expense but also accounting / bookkeeping for real estate / property management.