It looks like they have failed to make payments since April (we have been paying rent on time, auto-withdrawn from bank account).Ideally:  I'd like to have the loan/trustee waive all fees and interest, potentially lower the asking price ($10,000 discount on a $160,000 outstanding balance of a home that would likely appraise for $185,000) and we'd immediately go through the purchase process as is.Do I need to bring the Trustee into the discussion with the owner at the same time to make this deal go through?

There's no set percentage, but ideally under 30%.

Ideally before even getting estimates.  

Chances are extremely high that the Paul Davis, Servpro's, and Service Master's, etc. in your area do program work and are not independent.If I was in your position, I'd hire 2 independent firms who are certified by the IICRC in Fire & Smoke Restoration (FSRT certification) but ideally, have a Master Fire & Smoke Restoration certification.

Ideally I’m seeking short term debt with the plan of refi’ing them out after 6 months to a year.

Not ideal, obviously, but I try to stay positive in my outlook on investing in Pittsburgh. 

The above strategy you mention about helping borrowers get back on track is definitely the most ideal scenario IMO but you have to be aware of the fact that a good percentage of the time it doesn't play out that way.

I learned that the end of December was not the ideal time to purchase a property, as I was not able to take advantage of a property tax reduction whereby a tenant was required to be in place by January 1st to take advantage of this property tax savings.

Ideally - you would like to have a chat with your advisor when you acquire and sale a property.There are a couple CPA's here on Biggerpockets who you can interview with and see if you would be a good fit.

If you really like physics and engineering and talking about that, maybe teaching at the local community college would be ideal.