Are plan is to flip until we have the gain additional capital to increase our buy and hold portfolio.

In addition, you will need to collect sales tax/occupancy tax, if you do not and get caught, you'll be responsible for the tax. 

in scenario 3 you can pay tax or do 1031 exchange if you wanted to purchase additional property with the funds.Don't forget you'll be paying 25% depreciation recapture if you sell, regardless of how & when.I hope that helps.Good luck,Joe

What information do I need to gather from the agent / seller, and what additional due diligence do I need to do when evaluating this property versus when we evaluate SFR & Duplex?

I'm gearing up to make my first purchase and I think that my best move right will be to find a 2-3 bed room single family that I can live in personally and rent out the additional rooms.

The two most popular options seem to be using 15% downpayment if buying a duplex or by using an FHA loan that requires 3.5% downpayment plus additional fees depending on the total loan amount.  

They're all very busy, but if you can find a way to become valuable to them you may always have their ear.

Additionally, you have some marketing dollars to ramp up sooner.

I am currently witnessing the latter with my friend's addition(over 2yrs in the making). 

For example, if a borrower is refinancing a $100,000 mortgage, the closing costs will range between $3,000 and $6,000"In addition I found this, "The VA Interest Rate Reduction Refinance Loan (IRRRL) lowers your interest rate by refinancing your existing VA home loan.