Now both sides are long term rentals for me.

Yes you can as long as your father will live in the home as his primary residence and you put enough down to cover your portion of the loan that VA will not guarantee.Here are the VA guidelines for calculating the down payment.VA calculates the guaranty as described in the table below.Step Action1 Divide the total loan amount by the number of borrowers.2 Multiply the result by the number of veteran-borrowers who will beusing entitlement on the loan.There is usually only one veteran borrower, in which case the resultof this Step is the same as the result of Step 1.3 Calculate the maximum potential guaranty on the portion of the loanarrived at in Step 2 (as if that portion was the total loan).Use the maximum guaranty table in section 4 of chapter 3 of thishandbook.4 VA will guarantee the lesser of:• the maximum potential guaranty amount arrived at in Step 3, or• the combined available entitlement of all veteran-borrowers.5 VA makes a charge to the veteran-borrower’s available entitlementin the amount of the guaranty.If more than one veteran is involved, VA divides the entitlementcharge equally between them if possible.

I quickly learned that just because I signed a term sheet doesn't mean it's set in stone.

With some of the ones you wanted to put in a low ball offer, what did they end up selling for and how long did they take to sell?

Other finance options typically have worse terms. 

I couldn’t find a clear answer on how long you had to live in the “primary” residence. 

This is an exception.Theoretically you can have unlimite properties using VA loan as long as your benefit is not used up, but realistically no way you are going to keep on getting an exception.

I’ve already made some calculated evaluations in terms of the expected operating expenses, the mortgage, closing costs, and a 20% down payment. 

I'm particularly passionate about Long-Term Buy and Hold Investing.Outside of real estate, I enjoy Triathlon, Beer Runs and races, and pretty much any outdoor fitness type activity.Excited to learn and connect with you all! 

Make sure the contractor is tracking long lead items to keep the schedule on track.