For context, I will be assuming his VA loan at 5.1% and he will be doing seller financing for the remaining equity and sale price. 

Judges also postpone sale dates for buyers with financing, so cash is likely not necessary to get the date moved.

If you want to combine two or more lesser sales into one higher purchase that is fine as long as your purchase meets the timing requirements for each sale.  

Durham tends to offer slightly better cash flow opportunities compared to Raleigh, especially if you’re targeting neighborhoods that are up-and-coming but still affordable.

I just closed today on the sale of the second house and have ended the nightmare!

There's definitely some opportunity with people wanting to make moves post-storm.

Purchase price: $840,000 Cash invested: $75,000 Sale price: $1,200,000 Full renovation of all 4 units.

If no one but owner-occupants can STR... then that should mean opportunity for owner-occupants who STR their primary residences in many jurisdictions.- Large remodels or construction projects (Live in Flip) can be self-managed, worked on directly, and the value add, after 2 years, is largely tax free up to certain limits. - Many areas around the country allow for ADU Construction - house-hackers enjoy similar benefits to remodeling projects by being naturally on-site for ADU construction. 

That will put us into the long term capital gains category on the sale. 

Your plan can be something rough like: I own a piece of vacant land at (address), and I'm looking to rezone it from (current designation) to (new designation) in order to build a new construction duplex which will consist of  2 condos for sale, or 2 aparment rentals, eg.