I'm just following @Brandon Turner advice and trying to analyze one property a day so it becomes second nature eventually. 

The following applies in either an IRA or 401(k).The transaction you describe is considered a flip, or a dealer transaction. 

I would use this as an opportunity to get them all out.If one of the tenants wants to stay, make him apply and verify he can afford it on their own.

The idea is to consider the single-wide as the "primary" unit (that's how it's being sold) and apply for a construction loan to finance both the primary unit (the man home) and the future ADU. 

I would suggest you set up your key words in your profile regarding Canadian investors or Canada or something to that nature.

Be honest with yourself about what you will and won't be doing and then make sure you have people who can help you with the other aspects.I think its human nature to value what we enjoy.

In New York it seems that anyone can just apply and you have to accept them.  

We have a good cleaning team and handyman if needed.It isn't that hard really, but remember, your usage must be 14 days per year or less if you want to take advantage of all the deduction of expenses for running a vacation rental home.As far as loans go, we just applied for a 2nd home loan and that was that.

The third pillar applies after you have good insurance You need to protect yourself from what insurance doesn’t cover by compartmentalizing your assets.

I agree with Jay, $400k seems light for a full gut reno on a high end property in that area (although kinda hard to say without understanding square footage naturally).