He got married, moved out, costs have gone up, and he made a few adjustments, rented out the 4th bedroom and continues to hold it.

Where can I educate myself about the intricacies of buying from the Sheriff sale?

It's in a great area that will continue to go up in the long term even if it dips in the short. 

I would recommend looking into West Kensington, Frankford, and Port Richmond-  You can still find great deals there withe excellent cashflow, and I believe the path of progress will continue to march into those areas and increase values. 

:) But I’m brand new at this and just educating myself for the first time... so far the main criteria to finding a ‘proper deal’ I’m aware of is to make sure you but your property at a discount. (20% - 30% discount seems right but I’m sure practicing this is much more difficult than it sounds.) 

Additionally there are continuing education requirements.

It's somewhat surprising as prices for Mass overall continue on their tear as "last month the median single-family sale price increased 5.8 percent to $402,000, up from $380,000 a year earlier.

What else should I be asking or looking to educate myself on with respect to using my SDIRA to finance (lend) and hold a property for rent?

He was continually available and full of creative approaches and visions to help me find and get what I wanted in my life.

I’m sure you will do great if you continue to put forth the effort.Best wishes to you!