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Sportster? July in Kentucky, what kind of oil should I be putting in my bike ?What I mean to ask is, 10W-30 ?I'm at the 20k mark

 
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If you check with a dealer they will be able to tell you. I did all my own oil changes on my 1995 electra glide. I used 20w50 This is what the bike called for. As for synthetic a mechanic and very good friend of mine suggested not to put synthetic in until you have around 25 to 27 thousand miles on it. I started my synthetic after 27 and really like the change. My friend has a patent on his own engine as well as his own shop. Midwest choppers in antioc, WI. He is very good. Also at 35000 I started using synthetic in all areas of my bike. Crank case, Primary and trans. I'm thinking your sportster should take the same as mine did but a simple call will confirm what oil you should use. Sorry don't know for sure.

 
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what is the air temp?where you will be riding 20/50 i have found to be about the best all around for your air cooled v twin

 
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20W50 or straight 50W will do good to.