What wheel size and bearings should I buy for outdoor use?

For outdoor use, it is more about the wheel hardness than the wheel size. Wheel sizes of 57mm, 62mm and 65mm will work with these skates, just make sure they fit 8mm bearings as that is what the axels are. Wheel hardness you'll want to look for something with a durometer less than 84A. 78A is usually a good durometer to go with for outdoor wheels as they are soft enough to absorb the bumps and imperfections of the outdoor surfaces you are skating on, but still hard enough to roll smooth and maintain speed. For bearings, you can use the bearings that come with the skates, or if you are looking to get new or replacement bearings, you will want to go with an 8mm bearing. Our KwiK brand of bearings will work great with the R3 skates.

Would these skates be a good choice for a mid level jam skater? if not, what riedell skate would you recommend?

No, very uncomfortable for mid-advanced skaters, beginning is fine because you don't know any better, as I move into the jammer position on my team I notice these pinching the sides of my toes and rubbing really bad, the truck is plastic so you might want to invest in aluminum or titanium trucks. I recommend Bont skates for jammers or Ridell Vandal or Ridell 195 (low cut).

If I wear an 8.5 in women? What size would I wear in skates?

As these skates come in men's sizes you would want to order down 1 to 1-1/2 sizes and since the R3's only come in full sizes I would suggest ordering the size 8 and if there is a little extra space you could possibly insert an extra insole or wear thicker socks.

If i wear a size 10 mens in a shoe should i order a 10 in this skste

Men wear exact size. Since skates are all in men sizes. For woman they always the next size down So a size 6 in a woman's shoe, she would order a 5 skate. You would order a 10