Question
QUESTION: I live in Chicago.  I have a large tree in my backyard which make most of the area some what shady.  Every spring I apply seeds for shade with some peatmouse and top soil.  They either don't come out or die after few months even though I make sure I water enough.  Please help me.

ANSWER:  You say that the grass seed "don't come out"; I take that to mean that the seed does not germinate (well). Seeds will not germinate (well) if they are buried too deeply; or if they do not get enough water; or if they get too much water.
Small seeds do not have as much stored energy as larger seeds. Energy is needed to sprout and grow upward through the soil. For this reason small seeds must not be buried too deeply.
Water is needed by the germinating seed for it to grow leaves and roots. This water must be supplied until the seedling has functioning leaves and roots. A common mistake has been for watering to be cut off too early. Too much watering will cause the seeds to rot.
I do believe that watering is at the heart of your plant problems and I hope that I have given you enough information to get you better results.


---------- FOLLOW-UP ----------

QUESTION: When is the best time to re-seed.  Fall or Spring, for Fall re-seeding do I need to water enough to germinate before the winter frost?

Answer
Instinctively, I want to answer "Spring!" because the grass will germinate and grow into warmer weather. On the other hand there are grasses which go dormant in the winter. I really am not familiar with this phenomenon but I guess if you do plant such a grass early enough in the fall, it will germinate and get established before cold weather steps in. It will then go dormant as  mature (adult) plants rather than tender little seedlings which will die in the cold.
I hope that I have answered the second part of your question but let me emphasize that all seeds need water to germinate and all seedlings need adequate watering to establish and grow out. The germinating and the young and tender need short periods of watering but frequently. As they mature the watering should get longer in duration but less in frequency.