Harley 1340 EVO - What do?

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So I've owned a few bikes in my lifetime, including V-Twins, never a Harley. Guy is paying off a debt to me with a chopper he built. It's a fine deal by me as I have a lot less into the debt than even half the low end of what the bike might be worth.

It's got a 1997 Harley 1340 Evo engine, 3.5" Ultima Belt Drive (clutch), Ultima Frame, Screaming Eagle carb. Guy put it together in his garage in 2009, then medical issues so it sat there. When I saw it, I was surprised - this is a labor of love, it looks really nice, and although I don't know the engine history he spared no expense on bits and pieces and I'm satisfied it probably has no major issues.

Here's my question: I've never owned a Harley, much less this particular engine. I don't know the first damn thing about maintenance like I do with my cars. So, my questions immediately center around - what oil? What chain lube (I've only ever owned belt or shaft drive)? What general crap should I be doing and how often if I want to make sure this thing is treated right? I'll probably drive it 100 miles a week or so, with maybe a 250 mile round trip every other month. Florida, warm climate. 20W50? What's the best stuff these days? Is the Evo known as a "good" engine overall? What about that big-ass belt clutch on the side? Never owned one, don't even know what issues I may need to be prepared for when driving it to treat it right. Should I be using 93 Octane? Any additives to oil/gas? Anything you got, throw at me, please.

I'm so damn particular when it comes to my cars, I don't know where to start with this thing.