If interest rates start falling, and inventory doesn't see a surplus, I think you will see a hot summer of people buying and driving the values up. 

Either way, seller only receives their portion of wrap surplus, not mortgage PITI. 

I recognize there's a lot I have to learn, but I bring a surplus of energy and a hunger for knowledge.My day job revolves around design, and I'm excited to merge that expertise with real estate.

Can you time it to get your BK dismissed, sell the property and pocket any surplus proceeds before the creditors get a judgment against you and get a lien on your property?

Well, that would depend on state laws regarding who gets the surplus.  

Lastly, I want to be able to calculate surpluses and shortages per room or parts of the project.

Although the government has run a (now diminishing) fiscal surplus for years, it cannot borrow freely in international capital markets.

I would save all the pennies you can from your roommates rent any any other surplus income you have until you can refi,  but only if you can actually reduce your payments significantly.  

However, the cost might not equal value if you are creating surplus land for rather than adding to the highest and best use relative to the price of the additional lot.Get an attorney involved to ensure you are covering your due diligence.One item that comes up is if zoning/land use law requires to parcels under common ownership to combine to one parcel or be for the same use.

There is a short-term surplus of STR availability which I feel will be short-lived as new construction is not coming close to meeting demand from those migrating to the area.