That is an ultimate time waster and if I submitted such an offer I would not get any return calls from a developer, other retail brokerage, or other retail PM company in the future for my other clients.

Would it be the sellers responsibility to pay off that mortgage before the ultimate end buyer takes deed of the property or is that something the buyer could take care of, perhaps 50/50 on both ends?

At this rate, even accounting for vacancy, cap-ex ($30/unit/month), and a 5% reserve for a property manager, it's still an 8.65% cap rate, and (depending on the financing terms I ultimately end up with) will cashflow between $3.5-$5K a month.I got this under contract because of a combination of their realtor being inexperienced (She only listed it on one MLS service, not even in the correct county), the owners being burnt out (one of the owners tragically died in an airplane accident), and sticking to my strike price.

I always shoot first and aim later with my offers.The lease does not survive the transfer of the deed unless you want it too (I believe).

As for your questions, I'm going to give you a few resources that will give you the information you need.In short, yes you can rent the other side to a section 8 tenant considering you ultimately decide who gets to be your tenant.

Circumstances could change, there are different levels of insurance and education required for having your own brokerage and you may ultimately decide it isn't for you.

@Jeff Kehl  Ultimately I would like to have several larger properties under a larger C-Corp.  

I'm just trying to figure out the smarter course of action.Since this isn't really an investment property, and will ultimately just be a hedge against inflation, if I'm lucky, I'm not sure if it's worth the hassle of another move to the unknown.

My discussions/agreements have the tenant responsible for maintenance/upkeep, such as changing their own light bulbs and unclogging their own toilets, cutting their own grass, spills on the carpet, replacing things that become damaged due to their wear and tear up to $500, since they plan to ultimately purchase the home and will need to have a good appraisal for their own home loan, I ask them to care for the property as an owner would. 

The first step is talk to lenders, several of them so you can compare there loan programs (as long as they don't ALL run your credit score because that will lower it).Now you could use your VA loan to purchase a property with a rental built in and ultimately rent out both units when you PCS.