Hello,
As to your question about whether you will feel pain this time around if you were to have a medical abortion, no one can really say, as each experience is different. If you feel that you have a high threshold for pain and that helped you in your previous experience, I would think you might have a similar experience, although I'm not to sure.
As for surgical, I had one when I was 5 weeks gestation, I felt absolutely no pain because I was given IV sedation (they knock you out, this isn't general anesthesia). I went to sleep, and probably about 5 minutes later (thats how long a surgical abortion takes) I woke up in the recovery room, felt very mild cramps and had little bleeding (I bled for only half an hour, and all the bleeding was at the clinic, I didn't bleed again until my birth control induced period the following month). I never felt any cramping or pain either after I left the clinic. It really depends on the person and their situation, but I think I have a medium tolerance for pain, and this experience would probably be rated a 2 on the pain scale. Surgical is easier on you if you hate having to wait for things to get done, the longest part is feeling out the paperwork!
As for the sedation, like I said I woke up as they wheeled me into recovery, and was wide awake and lucid within seconds of waking up. It shouldn't last all day, but they say that if you have sedation, you should have someone with you to drive you. At the clinic I went to they required the driver to stay at the clinic until you were done . But most people find they can return to work the next day.
Hope I helped, and good luck!