I am Ian, I am based in Contra Costa County.

That's awesome your tenant is looking into options for home repairs.If your tenant needs any advice or recommendations based on my experience, feel free to share my contact details.

Estimated Rent (based on neighborhood median) = $2800Total expenses including HOA, Capex, Property Mgmt, and 50% rule for maintenance = $2750Cash flow = $50  :(Do I hold onto this gem or sell it and move onto a new strategy??

Aiming for a niche audience in STRs that matches your location is a good start. 

If so, review it to ensure it matches the estoppel certificate4.

While I have sufficient capital to undertake 1 or 2 flips at a time, the high cost of properties in the DMV area makes scaling challenging without resorting to interest-based financing.Is this feasible, or is it a stretch?

Establish connections with real estate brokers that focus on investment properties.Funding: Explore various funding options, such as partnerships, hard money lenders, private lenders, and conventional mortgages.Make use of your experience in building to precisely estimate repair costs and provide prospective lenders with well-prepared project proposals.Look into any grants or incentives that may be available to real estate investors on a local and federal level.Create a concise business strategy that outlines your objectives, both short- and long-term, target properties, and investment tactics.Remember, each real estate market is unique, so adapt your strategies based on your local conditions.

No because he is a corporation, based on "Inc." in the name.

Such as primary residence of an agriculturally based business?

I look at land sale comps (which aren't always easy to find depending on the state/market/area) and we offer something based upon the the retail value that land like that sells for.