Im really not concerned about this house but if we do more flipping in the future is this an actual concern?

My only concern there is that I do not see many listings for MF in that area and the ones I do see are very expensive.  

Therefore, if I'm looking to acquire a mutli-family property using residential loan terms and interest rates, my only option would be a duplex - and I am concerned that the cashflow on a duplex would not suffice to cover expenses and mortgage payments, especially given that I will be occupying one of the units to obtain the loan and 'house hack'.

When you structure a lease and option transaction with a potential buyer, you become a landlord as far as the "lease" side of the deal is concerned. 

Regarding what kind of cash-flow or ratios you need to retire and your concerns with future CapX, you should also plan ahead to have a reserve in the bank to handle the unexpected stuff.

Without a mortgage I could comfortably live on 1500/month and that includes having money for an annual sell-off vacation in the off-season to costa rica...Anyway, at 8% return I could RETIRE permanently on a little over 300k...However, that is in London, ON with a population below 500, 000 people (I think north of 400k?).

Stay on top of them to be sure they're not trashing your place and put them on MTM and the minute they are late, cancel their lease and get them out.We have higher end properties where I would never do that because they could stiff us for more money, but for the lower end ones, yeah, we'll do it.My only concern with dancer applicants is generally the kind of people they hang around, and the potential for visitors that are unwelcome or causing trouble at the property.

I believe one of my biggest concerns is investing while not living locally (although I do visit quite often) back home.  

My concern was twofold: First, you lose the ability to do the final walk through, because you have 60 days of not knowing what they're doing to your place.

What you can expect from Sherman Bridge Lenders: promises will be made to you, they will not be fulfilled; you will be lied to, you will be ignored, you will be stuck in a trap between the hard money purchase loan and the supposed refinance permanent loan you are ultimately expecting to get.