You may get lucky with a lender that allows 20%, but don't count on it.Your refi loan assumptions are unreasonable.

My other concern is that if I add a separate secondary dwelling, the property won’t appraise for any more than it’s at currently because my lender only counts 1 house, 1 garage building, and up to 10 acres in the valuation, even though everyone knows that 2 houses are going to be worth more than 1.

I took the time to break down all the categories from Jay Scott's book on Rehab Costs, and created a check mark spreadsheet that calculates category totals based off his suggested costs for each item and using any required inputs like sqft, item counts/costs, labor, etc.I then review the pics/video my agent sends me and go through my spreadsheet, checking off what I think needs to be done.

Now is where we count our blessings.

I have not counted on that and perhaps I should.

We are keeping our door count lower so we can give the best customer service. 

hard to count CA out .. 

Nope, on a couple of counts:1031’s are only for the sale and purchase of properties held for investmentA personal residence can’t be either propertyProceeds from a sale have to be used to Buy a property, not pay down debt

Rent it out after you move because 75% of the gross rent will count as you income.When you get to your next duty station you can use the VA loan again.Keep repeating the process

@David Serna this is great outlook. 12-18 month forecast looks good.Not sure if this is true, but should spark your interest, but I was told freelance jobs do not count in these numbers?