Is there a way to reduce that huge capital gain hit?

A good plan will show how to structure things like your wife’s business, potential rentals, and depreciation so everything works together to reduce your overall tax burden while transitioning away from W-2 income.

Reduce hold time by lighter rehab, getting deals that are smaller in sf, do not need landscape/exterior work (I.e. condos)4.

I have not done rent by room in many years but my son is currently doing it to live at reduced housing costs.  

.: We Use Lease/Options To Sell, To Reduce Expenses & To Increase ProfitabilityIt gets a little complicated so I'll try to make sense.

What are techniques a home buyer can use to get their desired price that results in a builder accepting a lower margin. Much of the guidance seems to suggest that buyers should be okay when they know margin is very high

A couple clarifications that might help:If you don’t do a cost seg and just put the buildings into service, then demo later, you can generally write off the remaining adjusted basis of the building as a demolition loss (since you didn’t buy it with the intent to tear it down - establish this).If you do a cost seg and take depreciation (including bonus), your basis just gets reduced by what you already wrote off.

Are there usually general industry clauses signed such that "if leasing takes more than 30 days then reduce fees to 0.5 months"? 

Reduced Vacancy Risk: If one tenant moves out, the others continue to pay rent, which significantly reduces the financial impact of a vacancy compared to renting the whole property.

Low down payment, reducing your housing expenses, building equity, learning landlording.