Given that you're not married, that adds some additional complexity.  

Very interested in the Cleveland/Ohio market in addition to a few other cross-border cities closer to Toronto. 

I'm terrified enough of doing this out of state, so I am not interested in additional complexities with BRRRR.

I would have contacted the locksmith tech to get additional details before assuming it was tenant damage.

https://nationalmortgageprofessional.com/news/study-reveals-....Not sure BP will allow that link to post, if not just google " 10000 saved using a broker vs direct lender" and you can find the article.On the flip side, there are some banks and credit unions that could offer products that they do not allow to be brokered.

I do have additional coverage for the sewer since I knew it may have issues before I bought the property. 

How do you finance the tear down do you add it to construction?

Ok it might not be 1:1 but it will add additional revenue.

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.

As for valuation, I see no reasons why a Junior ADU would negatively impact additional housing unit.