I wear contacts. I am at the point now where I can jab my fingers all over my eyes and it doesn't bug me. It takes awhile to get used to putting them in, but once you do, you can slap them in there with the quickness.
I put my contacts on after makeup, so there is less chance of something getting in your eye. If it does, it can migrate between your eye and the lens and cause discomfort or a blurry spot.
As far as the waterline, I still line it. Sometimes it gets my contacts feeling a bit goopy or looking a bit blurry. When that happens, I just take them out, rinse them and put them back in. Tip: Keep a bottle of solution, a case and a clean washcloth at work incase you need to clean or remove them at work.
The BEST contacts I have used are the Accuvue Oasys:
Buy Acuvue Oasys - contact lenses Contact Lenses from Johnson & Johnson Online at Vision Direct. They are amazing. Like butta! I had serious problems with contacts drying my eyes out until I used these. You can wear them for a few days at a time as well.
The most gentle and effective contact lense solution I have used is Aquify:
Buy AQuify Multi-Purpose Solution For Soft Contact Lenses Online at drugstore.com.
The last piece of advice I have is to not store your contacts in regular solution. Use one of these systems instead:
Buy Aosept Disinfectant for Soft Contact Lenses Online at drugstore.com. They thoroughly clean your contacts and make them feel great on your eyes. WARNING: Only use this stuff to store your contacts. When you go to wear them, remove them from the cage, and rinse them with Aquify before you put them in.
NEVER put AOSept directly in your eyes. It will burn like a motherfucker. How do I know? I was once in a rush to get ready to go out to dinner. I was dressed super nice, had a smokey eye and fake lashes. I accidentally rinsed my contact with the AO Sept cleaner and put it in my eye. It hurt so bad that I was on the floor. It hurt so bad that my body, as a defense mechanism, was holding my eye shut. I absolutely could not open my eye. Therefore, I could not get that damn thing out. I finally got it out, but my eyes were bloodshot, my smokey eyes were running down my face and my fake lashes were on my cheeks. Hot!
Hope that helps