He wakes up every morning at 4:00am and works 14 hours shifts.

And there can be pretty big shifts in the market either way after two years.

I am shifting my strategy from "buy and hold expensive SFH's in San Francisco" to include multi-family, high cash-flow properties within 2-hour flight or car ride from the SF Bay Area.

There's a post here that hits it spot on; good wholesalers will eventually shift to a strategy that gives them larger margins and selling to investors isn't ever the highest margin on a deal.I wholesale when the deal or price point doesn't make sense for me to purchase outright, which generally leads to crappy wholesale deals, unfortunately.There's a lot of people out there that have no idea of ARV calculations or costs involved at all, and simply think any house they put under contract is going to bet them thousands.

Once you have a couple of successful deals under your belt, the leverage will shift in your favor. 

Not going into a geology lesson, but the ground can rise and shift, peers on the interior of the footprint can move or sink causing many to think there are structural foundation problems, these can be an easy fix in old buildings.A bigger issue with a 100 year building will be asbestos, lead pipes including the water main, tile drains, lead paint, mercury and wiring.

Over time the risk is simply shifted from the insurance company to yourself.

They are a real issue, and there are a lot of houses with foundation issues (this ranges from slight shifting resulting in sheetrock cracks to heaving and worse).

I've since shifted my focus further south along I-5 (primarily the rapidly gentrifying Renton area).

I would shift my paradigm and look at opportunities to further leverage a successful investment I had held for 20 years.