Then we have 100k to invest into a larger property.

If you're trying to house hack, as long as you're going to be able to carry your property in the event rents fall by 5-10% then you'll be fine.The real worry is for investors who are buying larger multifamily properties and banking on most of their returns coming from a sale at a low exit cap rate.

But I've heard getting larger deals can actually be easier for funding, finding investors, etc.

I know this is sort of vague but we haven’t gone in to any real details on what they are really interested in just yet.

You can actually combine VA lonas with another person as well to get larger properties, but I do not think that will work in this situation considering you will not be in the area.My business partners and I over at Active Duty Passive Income are always trying to help military members invest in RE so please let us know if we can help.

There is sort of a driveway on one side but I don't believe it is wide enough to fit two cars, so the plan was to assign that to one unit. 

I would go see several lenders with all of the documentation sorted out and organized, then just present it to them.

He also has a larger 6BR 3BA house in Hopkins which he is renting. 

If we take into account the above assumptions that the deal make sense, in 30 years, when the loan is paid off, the larger deal would have generated a substantially higher amount of profit and net worth to the owner. 

Buying land to build anything outside of a stick built home is often too problematic thanks to the bureaucracy of the anti-development local government here...Perhaps consider buying a larger MFR with a partner down here?