This is always a popular question - and very heated at times, too. Just do a search and you'll get all sorts of opinions. Anyway, I own 3 harleys, 2 of them Twin Cams like yours. I've settled on this combo which works well for me: I use Redline 20W/60HD V-Twin oil in the engines. I just started with it because I was given 2 cases as a gift. Prior to this I used Mobil 1 V-Twin with success. I just came back from a 3000 mile ride on the Redline and no issues, quiet engine and I noticed that the oil temp never got above 230 in the hot days of 95degrees. With the Mobil 1 I would see 240-250 all based on the dipstick temp display however accurate it may be. For the Trans I settled on Mobil 1 gear oil 75W/90 years ago, works well and shifts are very smooth and less clunky. For the Primary I stuck with the Harley Formula+, also stick with the Harley 5 micron filters. You cannot use an EVO filter on a Twin cam or vice-versa.
You would be well served with M1 V-Twin since it is easy to get, heck I used regular Mobil 1 car oil in my old Iron Head sportster for 30,000 miles w/o issues. Still runs great today. If you want the dino route, I hear that Havoline 20W/50 is great - see fueltankerman's posts and UOA's.
One thing I can say for sure - stay away from the SYN3 oil as it is overpriced for the performance it gives. It'll be one thing to run it in the engine but don't use it in the trans and primary! I already did it, it is awful. ROugh shifts, clunky, etc. Even my local HD dealer is steering customers away from SYN3 in all 3 holes.
There, here's my opinion and it doesn't make it the best - just what works well for me and that's what makes this board so great - sharing information with others.
BTW - enjoy that bike!