Multiple people including myself have tried to caution him of the the true costs but he's been repeatedly dismissive and has made it clear we give him motivation and he wants to prove us all wrong (whatever that means). 

Time and practice will still teach you as you do deals but it will help you understand what things costs for the size of the property 

Quote from @Patricia Steiner: There are several lenders who offer low/no closing cost options for first time homebuyers.

You also have to ask about delivery costs and more.LABORLabor charges are trickier to understand, but Google AI to the rescue! 

It did not cost me $0.01.  

In doing so, bear in mind that the cost and admin of a corporation is higher and that the tax treatment is different:1.

VA loans are the only loans that allow this, and there is no rate penalty for it no longer being your primary home.With that in mind, you could do a cash out refinance today at a higher rate than current market rates which will create profit on the loan, we can take that profit to pay for your closing costs.

Which size of home is typically perform best on a cost benefit analysis?

I paid about $1500 in closing costs between title, appraisal, etc, but the original loan was wiped out in favor of a new lower rate. 

I agree with John, we are seeing renovation costs of $150k- $200k for a basement unit and $250k + for a coach house.