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?

You can buy back the Baltimore ground rent at a cap rate of 6% or negotiate it at a higher rate to get a discount.  

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.  

You would have to buy at a very deep discounted price like $40-50 cents on the dollar if u buying cash so these will have to be REO properties that need some cosmetic repairs for example I am buying  1 families out here for $26k cash (4beds 11/2baths )rehabbing for 10 k .

Never once had one redeem in all the years..Not to say there Is not a first time for everything :)of course if you can get the release pre sale this could be a benefit in two ways for the note buyer.One it could produce 3p bidders that would buy the note and if the OP bought it at a significant discount this could be a nice quick flip.. but if the sole intention is to gain control of the asset one MAY be wise to keep the IRS lien in place to scare off other bidders and risk the redemption that in all likelihood will never happen..