Stereochemistry is different enough from normal organic chemistry to warrant its own article. The best approach I found to stereochemistry is utilizing the Organic Chemistry as a Second Language, Chad’s videos, and lots of practice problems. Information on these can be found in the Tools for Organic Chemistry article.
The first time I truly ‘got’ stereochemistry to the point it stuck was after watching Chad’s videos, taking notes, and putting the examples he draws on the board into the SRS. His explanations are extremely helpful and his examples are clever.
Memorizing examples in the SRS finally made stereochemistry ‘click’ for me. When taking the DAT my memory immediately shot back to the examples in the SRS and it became easy.
Basic Stereochemistry Fact
This model is similar to a regular basic fact.
Front: The highest priority group has the […] atomic number
Back: The highest priority group has the greatest atomic number
Front: SN2 reactions […] stereochemistry
Back: SN2 reactions invert stereochemistry
Front: […SN] reaction creates racemic mixture
Back: SN1 reaction creates racemic mixture
Front: […] mixture is a mixture of R- and S- stereoisomers
Back: Racemic mixture is a mixture of R- and S- stereoisomers
Front: Racemic mixture is a mixture of […]
Back: Racemic mixture is a mixture of R- and S- stereoisomers
There will likely be less basic facts than examples given the visual nature of stereochemistry.
Example Cards
The bulk of stereochemistry. Again, Chad’s videos have great examples and I recommend watching and pulling those.
Front: 
[…]
Back: 
Diastereomers
Front: 
Which C is chiral?
Back: 
Which C is chiral?
4 different substituents
Note the use of an extra note. This helps sometimes to ensure the answer was reasoned correctly.
Front: 
[…]-Configuration
Back: 
R-Configuration
H in front inverts answer
This will handle stereoisomer information. I believe the practice problems and SRS together quickly build a strong understanding of stereochemistry. Also, Chad’s videos!