If your buddy has the means and desire to bail you out if/when Murphy’s Law comes into play and the rehab costs twice as much and takes twice as long as expected, or the appraisal comes in low, or an unexpected capex issues arises at the worst possible time etc. then maybe do the deal just to get one under your belt, but it seems pretty risky and there are a lot of ways this deal could end up being really bad for you.

Homestead exemptions reflect the equity arising from the thinking in of English Law as to equity.

So would be happy to refer him if the time and need arise,,, helps to have someone that is tight with the inspectors

What I see in L.A is that a rising tide lifts all boats.

If their car is in such bad shape, maybe they don't have the money and/or inclination to take care of the property if a problem arises."

This may sound straightforward to most but I would like to know being a Canadian Citizen, if i wholesale (assign) deals in US using my US Based LLC, are their going to be any tax liabilities arising out of those transactions?

The risk here is that you are buying from a semi-anonymous seller, so there is no trust and no relationship to fall back on if problems arise after the purchase. 

A business entity structure which can shield you from liabilities arising from your RE dealings is much more effective.

I'd be crazy to think that new models wouldn't arise, but I certainly don't know what those models are (just like I couldn't predict new methods of communication (the Internet), new methods of shared transport (Uber) or new methods of short-stay housing (AirBnB)). 

Is that saving worth it, vs all the landlord/management issues that will arise while you wait for the magic of appreciation?