There are good enough directory submission softwares available (free and paid both). I recommend you to submit your site manually with different titles and different descriptions to web directories. That is best option IMO. DON.
Manual submission is the way to go. If you want to save time, you can use RoboForm or some other form filler. I will not recommend auto-submission.
Manual submissions would ensure that your sites get submitted to the right category and also that the submissions go through just in case human intervention is required when an error shows up.
No softwares in this world can compare with quality of manual submissions. I agree that manual submissions are slow, but worth value. Just remember to use various titles and descriptions everytime you plan to submit your site to dirs. Happy link building
But what if we are owners of 20 different directories and want to submitt one client to all 20. It would take a long time to do it manually. If we know our categories why can't it be automated?