Now the secondary question that may indicate a superior skill level is:  is the market bearing the filter? 

I’ve been fantastic in the past at developing quick relationships and I thought this skill would fit wholesaling.

Those are great skills you developed.

If a rental the building inspector will reinspect every year to verify it is safe (At their whim, smoke detectors, handrails, step height a little high this year, crack in cement, flowers don't jive with the neighborhood "aesthetic". 

Although, there may be certain barriers to entry in larger multi families (team, resources, skill sets), I agree that the same effort (hard work, consistent action, and resourcefulness) is required in any sized property.

My expected numbers on the SFH (without the new roof) are below:Purchase Price: $155,000 cashARV: $300,000 75%: $225,000REHAB: $70,000Should I add the new roof for the overall aesthetic of the home but more importantly will this raise the ARV to help accommodate the extra rehab expense?

Plaster is easy to repair, but it requires practice to become skilled at it.

And then you have those creeks, which have the best prices around them because they are not very aesthetic and I guess neither very safe.

What skill set does the current owner have?

First the Bay Area:   This region had the best economy during the last real estate cycle and the region has the most innovation and some of the most skilled workforce in the country.