Ok, I would go with a RK classic, nice look, hard leather covered saddle bags, you can put on a back rest and rack and take the the stuff you need for your trip, when you want to cruise open style, you can ditch the backrest, windshield and have an open road wind in your hair crusier. I had on the fly adjustable air shocks on the back. a jardine rider backrest that could move to passenger backrest in seconds. and all the room you need on the rack for packing extra stuff. Now when I was at bike events, it took about 10 seconds to take off the backrest, windshield and drop the back 2" for that low ride "look", transformed from touring to street in seconds. A bobber is nice, for bobbing around town, but you're gonna need to take some stuff with you. and all that wind for several hours a day, for me, that get's old real quick, but I can tell you, you will get wind, rain and anything out there, the windshield will help cut down on it, but not eliminate it. The ride, well, it's a harley, it's gonna make noise, vibrate, etc. it's not going to put you to sleep. too much of a good thing no matter how comfy is not good. you're gonna git saddle sore once in a while especially riding for hours and hours a day. I would also consider, what gear you gonna take with you, make a list, figure how to pack it and the best way to balance it all. I have a friend of mine, she's 90 Lbs, soaking wet 5'2" and she rides the heck out of her road king, even with her boyfriend 6'2" 200+ on the back, so if she can do it, I know you won't have a problem. One down fall I can tink of for the bobber or classic, spoke wheels, look great, but not tubeless, so if you're out in the middle of no where, you can't patch it and keep going. Tube less tires and a patch kit should be on your list, it will at least keep you going down the road. What ever you decide to ride, you're going to love the experience, all of it. Best Tom