I recognize there are other ways I could invest this cash (including another property) but I am being mindful of levering myself out too much in the current environment where job losses are more common in my industry (tech).

That amounts to a loss of $6240 in cash flow per year.2) Property Tax discount of $466 per month is for the first year. 

Chalk these losses up to tuition. 

It's very easy to make one tiny, minor assumption to fill in an unknown that completely changes the context and consequently the answer - I've caught myself doing this a few times.As far as the legal responsibility for the debt goes with Subject To, my guess would be that the contract basically provides a pathway for the seller to pursue the buyer for recourse related to losses they suffer from the default of the original loan, like a form of indemnification, but does not absolve the seller of responsibility for the debt.

Start simple or go all in on a multifamily if you have the capital to support potential losses.

Additionally, they made the argument that, as a large company, if something went sideways with an investment, they would cover the losses.

Repairing to sell might recoup some costs, but given the market and your limited funds, selling “as-is” is likely the best option to minimize further losses.

I think behind tenant screenings and leases there is a quality of a landlord that's also as a person that is the respect for a good person and the intelligence of making fair affairs.
For me for ten years in the past...

Trying to cut my losses as the borrower got all her unsecured debts discharged through Chapter 7.

The days we knew back-when have been sadly mostly lost, to the loss of everyone.