Hi and welcome to the forum!
I'll try to answer your questions as best possible, in my usual rambling way:
1. How much of a drip/leak from the centerboard handle is normal? The current rate doesn't seem concerning, but does any leak at all call for a replacement gasket?
All boats leak, what matters is how much you feel like bailing! The centerboard swings on a square "axle", which goes thru a hole on the starbd side of the trunk and the handle screws to the end of the axis. There's that big triangular frame that holds the starboard side of the axle and also presses the gasket into place against the hole in the CB. So, if I were you (famous last words), I'd start out by simply tightening the three screws holding the triangular frame to the CB Trunk. Be careful, though, when I was removing my CB I managed to sheer one of the bolts - they are probably original, 58 years old on your DS, go gently. OTOH, you're gonna have to remove those screws if you want to replace the gasket, so no added "risk" in trying to tighten them first.
2. What is the usual main sheet "traveler" set up on a DS1. It's hard to tell from photos online. At present, the setup doesn't allow the main sheet blocks to move along the traveler line, and I'm OK with that cause the alternative is a traveler that is basically always at its leeward limit. But is there another way to rig it so that it functions like a track traveler and can be used to pull the boom to windward?
You are planning to set up a boom vang, right? Make sure to set one up with at least a 12-1 purchase and read the posts here on this site about "vang sheeting". With a good vang, you don't need to pull the boom to the windward of the centerline. Remembering, the whole reason for pulling the boom to windward is to control mainsail twist. A good Boom Vang does the same thing, just better. Anyway, read here re: traveler, is how I set up mine - it has two settings "short" and "long", otherwise I use my vang:
https://forum.daysailer.org/tech_rigguide.phpBy the way, unless you are racing, ditch the Cunningham, rig a boom downhaul. Just my not-humble opinion, of course, but why screw around with the luff when you can just pull the boom down? Capt Briggs Cunningham invented his eponymous rig specifically to circumvent the racing rule forbidding boom downhauls. So, if you're not racing, why bother? That being said (written), be aware that space is at a premium between the boom and the cuddy top. Between boom vang, reefing gear, halyards, etc, there's a lot going on in very little space. A possible help - on my hinged mast, I mounted a D-shaped Boom Bail on the aft tabernacle pin, and the boom vang goes to a snap shackle (mind the mean working and breaking loads!) which rides on the Boom Bail.
3. Does anyone have experience with a half-decent rowing set up for a DS1? I know it's never going to be that fast, but could be more efficient than paddling. Basically, it would be nice to cover that last half mile or so without an engine when the wind dies.
No experience, just research from when I was considering oars (prior to my present electric outboard). You need at least 8', ideally 9' oars and you need to put your oarlocks on small risers (1 or 2 inches) to clear the rubrail. You'll want to sit on the Centerboard thwart, which for a 1966 boat means you'll need to build yourself a little "stool" to clear the top of the CB Trunk. Also, check out these videos (prepare to have mind blown, expedition sailing a DS2 off Labrador):
https://youtu.be/4TXjzoilnwU?t=420Here's a view of their sliding seat, talk about overkill (handy for expedition, though):
https://youtu.be/Mm8xjwYqR_U?t=239Anyway, both short clips should give you a good idea of how to mount the oarlocks. I like that their oarlocks also fold out of the way, although you'll be just fine mounting/unmounting them when you row. Make sure to put a good stout and long backing plate underneath the oarlock mounts! Spread the load over as much of your side-deck as possible.
Love the Penobscot Bay! Where are you sailing out of? I've sailed over around Deer Island, but never the West Side of the Bay, too $$ for me anyways....

One of these days, though.., would love to launch at Rockland and sneak over to Vinalhaven. The Basin/Granite Island fascinates me, if I can time the entrance right. One day.

Fair winds!
Tom