I've sent a letter to the family attempting a sub to, but with no response, it is looking like a trip to the sherrif's sale. 

Also, you cannot engage in real estate negotiations on someone else’s behalf or even attempt to conduct a real estate transaction for another person or organization unless you are properly licensed.Source:  http://www.criminaldefenselawyer.com/resources/brokering-real-estate-without-a-license.htm

The agent finally got back to me after many attempts and notified me the properry is now under contract to another investor for $1,100 over asking price.And Will, we're on to the next one!

I would discourage you attempting any option besides hiring a contractor to rehab like your original plan. 

With respect to that, I am attempting to balance the JUMP IN NOW urge with the 'analysis paralysis' BTurner and JDorkin refer to in the BP podcasts.T-minus three months... goal/deadline for going under contract on an investment property.

As I do so, and attempt to crunch numbers and look at listings for practice and to get a sense for the market, I'm running into some walls in my theoretical business plan.I will have the resources in the next few years or so to get a conventional mortgage on maybe 4 single family homes that are worth about $200,000 each, standard 20% down.

dont even attempt it. 

I studied Wholesaling for months before actually attempting it.

In Mr's new plan, his attorney attempts to drag the 2nd out over 5 years.  

After spending 35 years in the brokerage industry ( stocks and bonds)  I am attempting to add rental property to my portfolio for diversification purposes.