@Levi Giafaglione  I just stumbled across your post re: shipping container home and  land purchase three years ago. 

The problem with ACV is that, on a partial loss, the claim, under an ACV basis, has a deduction for depreciation.

Higher monthly payment - this is simply due to both the added monthly PMI mentioned above (which I believe is also not tax deductible like mortgage interest) and the fact that it's a bigger loan size because you are putting less down. 

Where I am struggling is when you take into consideration the tax due because the CRA taxes you on taxable income (where the big difference being that you can only deduct the interest portion of the mortgage payment so even if you cashflow positive, you have negative earnings after taxes), I find it very difficult to make the math work unless you put high % down payment.When you invest in Canada, do you only look at cash-on-cash return or because of the tax treatment in Canada, do you look at the taxable income as well?

Real estate is expensive, repairs are expensive, and if you don't put much down your cashflow won't help out all that much. 300 bucks a mo doesn't do a lot when you have a 1k bill for new water heater that just died or an insurance deductible or people just stop paying rent and you have to evict.

There is a great strategy to not get caught up in the franchise taxes levied on California LLCs by segregating assets into trusts. 

What about owner occupy, or family.If you are a broker or real estate professional you can qualify to deduct passively up to $25k per year on RE activities.https://loopholelewy.com/loopholelewy/01-tax-basics-for-startups/passive-activity-rules-01e-rental-real-estate.htmAlso depending on how much you make you can deduct alot of expenses, look at accelerated depreciation that might help.You have to look at least a 1 year hold that will reduce you some and is the debt service more or less than the tax hit.

I think mine is getting overwhelmed by it all, missing some major deduction possibilities in his rush to make the extension deadlines.

On the plus side, the QBI deduction in the recent tax bill will save you some coin.You should have SOME type of corporate veil (move it to a corporation) to protect your personal assets as well as create barriers between the properties where necessary, but the specific solution to your situation is a bit too vague for anything other than generalizations without more clarifying information, and your best and most specific advice will come from a local and trusted tax advisor and/or lawyer. 

:)CheersLucasThere is no Limit on expenses you can deduct.