First Time Short Sale - What do I need to know?

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Hey everyone - really need some help and fast!

I've been working on a lead for some time now, they owe a considerable amount of money. For some reason I never considered pursuing a short sale until the seller reached out to me saying that another investor wants to buy her TWO homes with a short sale (on one home they are behind on their mortgages, taxes,  and a few other small liens; on the other home it's just the mortgage and a small amount of taxes).

I have a very good relationship with the seller so that gives me the upper hand so long as I can make moves quickly. Time is of the essence. That's the problem though - I do not have a lot of time to act and I need to prove myself to the seller by making tangible progress (an offer, etc.) but have not performed a short sale transaction before.

From my understanding, I will need to reach out to their lender and see if that's a possibility. Is that my first step? What else can I do to get this moving and lock her in to dealing with me?

I get WHAT the process is, but am trying to understand the HOW behind making it happen. Looking for any advice.

For a little more background... the one house is problem house, it is a full gut and practically worthless (they owe 25k, ARV around 100-110k) and the other home is in fantastic condition, ready to be rented (they owe 20k on I believe at 228k mortgage, home can be resold for 260k give or take, or rented as it is in a highly desired neighbourhood).... Multiple people have started reaching out to her so I feel like there is opportunity at the right price