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I'd recommend the K75 also. The K100? A "little" more vibration? HA! That thing will put every extremity of your body to sleep! To Avoid. I have an 87 K75S I bought new, still lovin' it. Just recently BMW came out with a bike that may some day replace it, the K1200GT.
I agree the standard K75 line may be a bit tall, I am at 5'9" and still seems a bit tall, but if you brake properly and NOT let both of your feet pop off the rests when stopping (use right foot to brake to a stop), you will find it is easy to get used to (put down left foot only). This should hold true for any tall bike, within reason.
Problem with the "low seat" K75 is the seat is also rather thin, kind of wraps around the frame tubes, you'd probably be happier with the standard flat seat. I have a Corbin, which is actually a bit taller than the stock seat.
I really love the looks and handling of the S, but if you think dual-sport is appealling, you'd want to remove the chin spoiler. If you remove the bracket they look OK without it.
It doesn't seem like the Milwaukee Iron is holding it's value more than anything else these days, market is getting saturated with them. Used to be, here in WI you hardly ever saw an HD for sale in the papers, now it seems 3/4 of the bikes for sale are HD. It will be interesting to see what the future holds for HD. After the old school loyalists die off, can they really compete? The only thing really different they've done is the V-Rod, which I kind of like, even road-tested one, but it doesn't give me the old HD feeling, I've ridden plenty of them, never would own one though. Just not a V Twin fan. Damn Milwaukee County Vibratory Ailments....... I agree not all of them are all chromed up, just MOST of them. Probably about the only HD I'd really like was that Cafe Racer, a neighbor had one back when they were new, what was that the XL1200CR? Somethin like that. A friend also has an "original" Sturgis, the first HD with belt drive, I think it was just the secondary though.
By bro's both have Electraglides.......
Gilly
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