I like a nicely done slotted headstock. As for stringing them, I put it in the same category as tying on strings. The 1st couple of times it was watching Youtubes and painfully slow (does the tail come out left or right, how do I thread the last tail the other direction so all tails are held under the tie of the neighboring knot...). Now I don't even think about it. I've heard the discussions of string break but it doesn't make sense to me at the nut. A good string break at the saddle puts downward pressure on the bridge which disperses it to the soundboard. But how does more pressure on the nut help anything (except for maybe Blackbirds with hollow necks)? I do prefer the look and function of backwards facing tuners over "ears", and find tuning easier. But would I pay extra for that, all things being equal? Probably because as I said, I like the look and all these things together make a difference to me. Would I not buy an excellent uke because it has a paddle headstock? Absolutely not, my uke family is probably 60% paddle, 40% slotted. But if I was getting a new uke made to order, it would have a slotted headstock. At the end of the day, it's a look, just the same as a cutaway body (except for 2 or 3 famous players who play up there). And with looks, some like them and some don't. Oh and as for best looking slotted headstocks, definitely I'd vote for the Kanile'a long, thin cobra model with the Gotoh Stealth tuners!
Which brings me to a cool side story, I once bought a Kanile'a Diamond model super body with a crack in it (priced accordingly). Took it to my luthier to get the crack repaired and when I went to pick it up he wanted to give it a buff-out on the buffing wheel. While he was doing it, the wheel grabbed the uke, pulled it out of his hands and slammed it onto the concrete shop floor. Smashed the beautiful Koa body into a million pieces. He felt so bad, all the years he'd buffed guitars, never had a problem. But the neck was untouched. So instead of paying me for the destroyed uke (which I never would have let him do... we'd built 2 guitars and 1 uke together), I told him I'd like him to work with me to make a new body and attach the Kanile'a neck. He had some great bear-claw Adirondack spruce and I had some Ziricote I had bought for my next build. The result came out great and sounded wonderful. I named the uke KaniRick'a
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