Got mea PSE DeerHunter 2009 Model this weekend at Basspro.
I am already setup and had some fun shooting Yesterday.
Plan on Spending a fair amt of time learning my limits..

How did everyone know when they were ready to hit the woods.
What feeling came over you that made you know.

Months of practice!

From someone that just took up bow hunting last season, practice is the best advice I could give. Not just standing in front of a block target, but practice shooting in weird positions. Practice sitting down, practice kneeling, practice twisting your upper body around and shooting this way. Maybe find a 3D shot to shoot in. Then when you can hit at known distances, practice at unknown distance to allow you to practice at judging distances. (this is my biggest problem btw!) Figure out what you and your bow are capable of and then have at it. The best teacher is going to be the woods and the deer.
Also, if you haven't already find someone who has been doing this for a while and practice with them. Form is very important. You can practice all you want, but if you are practicing bad form, it isn't that great.
But to answer your question, I don't know if you really know when you are ready. I shot a bow for about a month before season last year and then just went. I didn't harvest a deer with a bow my first year. I learned a lot and had a great time. Now this season, I have two in the freezer and have let a lot of does walk. Just waiting on a buck to make a mistake now!
Have fun and just do it!
Good luck

being able to nail a baseball sized circle at fifty yards nine out of every ten shots. of course the new bow i got helped there a lot. but just find a range that you feel comfortable at and make that your limit. don't exceed it. i just got started last year but i've figured out a 3d target and a live deer are two completely different worlds. practice and be prepared. thats the best advice i can give