When I go in to "make ready" this spring, I still may be losing a little money. 

Send a professional letter with your typical we buy houses message, then add a handwritten font at an angle that says "If you don't want to lose the monthly income from this property, we have options!".

I bet this property would lose $200-400 each month.

If you work hard for it and it goes down you lose time and money.But that depends on the risk profile you have for that money.Look at the Delta between your options and asses your risk of loss against it.

I hope you're not losing track of your dates... earlier you said DD was until Monday but now it's the 18th? 

You can lose money either way but your downside risk is *usually* lower the lower you start on the ladder.

You can drop the price even if you break even or maybe lose a little bit that’s better than losing the whole thing.

If you lose your job or the heater fails in the winter, you dint have a landlord to come fix it.

Purchase price: $50,000 Cash invested: $30,000 First deal, had to pay seller's back taxes so she would not lose the home before I could purchase it.

For example, things like: how far behind (how much $) their tenant is behind on rent, likelihood the tenant would ever be able to catch up on their own (without assistance), whether the tenant is collectible should the landlord decide not to pursue assistance and go after a judgment in small claims court instead (some tenants are judgment-proof so the assistance may be a better option), ability of the landlord to weather the storm (do they have a lot of reserves or are they about to lose the property), willingness of the tenant to cooperate in the process (you need the tenant's cooperation for this to work), etc.