It is also a classic case of the metrics not telling the whole story, without some additional digging.Spartanburg and Greenville counties are on fire, everyone knows this.

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?

When you go to sell the property in the future, any depreciation take over the years reduces the cost basis and will also have to be recaptured as ordinary income, when you are likely to be at a higher ordinary tax rate.

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.  

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).