However, that does not mean there isn't just as much risk.Before we even talk about numbers (and the fact that a 100 year old house with a new roof is still going to have many repairs come up), I think the first question would be how much experience does your buddy have? 

I typically use 0.8% of the property value as a starting point, but this will depend heavily on the age of the roof and the structure type and age, as well as deductibles on wind and hail. 

However, the CRA treats LLCs as corporations, meaning you could face double taxation—once in the US and again in Canada at the personal level when the income is distributed.Typically, this issue is addressed by establishing a holding LP or LLP and then using single-member disregarded LLCs that are wholly owned by the holding LP.

So I think I messed up when establishing this LLC and chose for it to be treated as a partnership.

This is what Burger King does: McDonald's spends millions in researching the best areas to establish themselves in a city.

These relationships are essential to establish.  

Establish a wide safety buffer so you aren't broke at 80.

I believe it's more for established "housing" ie a caretaker that has elders living/renting in rooms, halfway/sober living units, things like that.

Lets say my first potential flip is from 1900's, has 4 layers of roof shingles, outdated electrical, needs a new kitchen, plaster down/drywall up throughout the house, flooring, and a terrible, terrible foundation.

-Start with a JV structure on a few smaller projects to establish a track record before seeking full financing on your own.