@Matthew Sarro - Thanks for sharing your journey—it's clear you've got a solid foundation with your experience in REITs and hard money loans.

If egress is already available, great, but often times this means digging an egress "well", structurally reinforcing the foundation where the larger window will be going, etc.  

Built me up then in a blink of an eye shot me down.

Wholesale/Off market - These agents or wholesalers provide the best deals to proven investors first, the ones that they have built trust with have proven themselves.

You would need to ask contractors.You buy something already built and renovate, you get tenants in and start making money that much sooner.

He has acquired the land, gotten the permitting, has construction financing lined up but needs ~20% cash equity / home.I know very little about his particular real estate market, and I've never built anything myself. 

Right now we are seeing land taking some decent hits (especially what your selling) as disposable income is down and a lot of this land really has no way to be built upon because it lacks any source of water.

It appears there may be a built in bias in the spread between acquisition and sales price by appraisers and underwriters.

True wealth is built over time.

He has a good job but no savings built up.