"It really can't be this hard"

No it can't be.  When I first purchased ProSeries back in 1942 I believe, I opened up the software and just fiddled with it and found it was pretty easy to navigate since it is form based.  Between being able to work backwards from the 1040 using the little magnifying glass to find where to enter stuff and the little green "where do I enter" button, it is pretty user friendly as to data entry.  As a side note, if you have called support several times, I think you have called support more often than I have in all of the years I have been using the software.  It sounds like you are trying to learn how to swim by only sticking your toes in the water.  Go ahead and just jump into the deep end of the pool -------------- it can't be more than a couple of feet deep --------------------- you won't drown.