Chalk these losses up to tuition. 

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

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.

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

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.

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

@Seidy Lasker Wash sale rules apply to stock options if they are deemed "substantially identical" to a security sold at a loss within 30 days, such as options with similar expiration dates or strike prices.

But because he raised rents each year, and rents were increasing by ridiculous rates, tenants constantly moved, had to sell the property at a loss several years later due to constant vacancies.Finally, the most interesting situation I ran across was a tenant, a 93 year old tenant paying rent on a 2BR apartment for $90/month.

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