Landlords are very motivated people given the right circumstances.  

One other strategy, might be hard to get, but a letter of support by your city fathers, representative, zoning board, official types for the proposed project, the Kroger guy can help with that, Freddie won't be bucking this transaction if you need to give title for them to proceed in zoning, IMO, just a little political flavor to the reality of your circumstances, that shows you will likely be moving anyway.

I'm thinking about going after short sales for flip or buy/hold properties--but the often-lengthy process gives me pause.  What happens if I make an offer, but the wait is so long that during that time I've found anot...

Financially, I probably leave a little on the table, but it's far far less time, and that is what makes it worth it for me as a part-time investor.The lowest below market that I have ever gone is 20% - but that was a special circumstance and not something I would advocate.

We are negociating a 15,000 dollar post closing security escro in which I could use these funds at my discrection to make needed repairs that the seller has otherwise neglected.

@Gregory Jimison depending on circumstances it could be the same day.

Put your efforts into one and neglect the other, especially that studio conversion.  

It's not so much what market aspect you begin with as much as it is the type of property, the circumstances that exist before you begin your approach.

Does it state that tenants are responsible for neglect?

We like the idea of making neglected properties better places to live as well as more profitable.