I'm not going to offer advice because you shouldn't compare yourself to any other pilot. I doesn't matter what someone else would do, they aren't with you. When you are in the airplane, you alone are the commander and will decide the flight's destiny. (That's why you log PIC time.)
I suggest you should sit down with a personal minimum checklist and think about what recent experiences you need to make yourself feel comfortable for this type of flight (and others). The checklist will help you define a box that you can safely operate inside of, and you can expand the box as you gain more experience or shrink it due to a lack of recent experience. If you think about what weather, currency, training, etc. you want to have while in the comfort of your house you won't be pressured to make a bad decision when you get to the airport and haven't thought through some of these situations.
http://www.faa.gov/education_researc...0checklist.pdf
After you fill it out, you should sit down with your CFI and have him review it with you.
Blue skies,
Rob