Seems like you are going to head in the direction of cruiser with the reference of the 883. Keep in mind the pricing of Harley, also that the sportsters are top heavy and not very low to the ground. I am in no way knocking harley, i was even looking into a sportster (used) when i was bike shopping. I just found them too tall and narrow and top heavy. I like to sit low and have a low center of gravity. I cant afford that 'comfort' on a harley lol. This is why i went for japanese cruiser. Also, the 883 is 5 hp less than say my spirit 750 believe it or not. But if thats what you want, by all means go for it. They just werent my cup of tea, for others they are excellent.
Honestly, Honda has the best built bikes in the cruiser catagory. I seen it over and over in reviews how reliable honda is. If i were to sway you ... i would say go for a Honda. They also have a huge following on the net (forums etc).
I will say it again, the only person who can pick a bike out for yourself is YOU. Just like i said above, go sit on as many that interest you. No two people will find the same bike comfortable to them. I sat on a bunch i really liked the look of only to find the pegs were too close to me, handlebars too 'bull horned', headlight too far into my view...things like that. Every bike has something 'different' about it making it a 'job' to find what fits you best. Remember, its your butt that has to sit on it on long rides!
As for cruisers taking turns too wide because of going too fast into it... well, that would be rider error. If you wide out on a turn because you entered too fast, then shame on you. Entering corners with a cruiser is like any other bike, set it up before you enter, sweep the corner and accelerate out. Theres no reason you should take a corner wide like that unless you are doing it wrong. I have no problem tearing up twisties on the Spirit
Peg dragging, unlikely unless you are tearing ass on twisties leaning that bike for all its worth (remembering that most tires will only take 1.1g's before letting loose while leaning). Pipe dragging, no way. Show me a bike that the exhaust is lower than the peg on a lean and i'll eat my shoe (minus those lowrider customs that are 2" off the ground). Thats why pegs lift up, so when u do drag one, you just pee your pants a little bit lol but you wont lift the bike off the tires. I am no maniac on twisties, and i've got some major twists around here and never come close to dragging a peg besides 90 degree turns going 10mph. Even then, im probably an inch or two away from dragging.
As for having to stop all the time on a cruiser: I've ridden my Spirit on 100+ mile ride arounds just getting myself lost without taking constant breaks. I may stop once for a drink or a smoke break, but very rarely because of being uncomfortable/in pain. Now, my $450 mustang seat has alot to do with that obviously, so you will want to change out seats or find one with a touring seat already on (much cheaper that way lol).
As for plugging my bike to give you a personal opinion, sure i can give that a go. I would have to say that after all the looking i did, sitting i did, research i did that the honda line just stood out above the rest. I love my spirit. I really like the feel of the drag bars, so that i have to lean a little bit instead of sit up holding onto bullhorns. I like the factory forward controls because i can stretch my legs out a little better (i also put 4" fwd controls on it, i can put my legs straight out now if i position them just right on the highway, VERY comfortable for me). I really like the liquid cooling mainly because i live in town and there is a stop light every dam block. Works great when i am in town riding around. Liquid cooling was a BIG seller on my list of 'wants'. I wanted shaft drive for the low maintenance and quietness, but spirits are chain, so i took a loss there (although, the 07s are now shaft, yet they are air cooled now lol. one step forward, one step back). I like wide bikes, the shadow line sure takes care of that area. Chrome, i cant get enough of it. The shadow has more chrome on it than just about any other bike on the market (w00t). That saves me alot of money not having to buy chrome replacement parts. I like LOUD bikes, aftermarket pipes were also on my list of 'wants'. I took the baffles out of it and its about as loud as any harley out there. Accessories: again honda kicks ass in this dept. Yamaha also is VERY good with aftermarket parts availability ( i almost bought a vstar because of that ).
Personal preference, i will probably be sticking with Honda for a long time to come. Whenever i decide to move to another bike, it WILL be a Honda 1100 'something'.
Again, keep us posted on your progress! Me an bob will surely help out answering any questions you have (and possibly arguing which is a better bike LOL).
PS: ive dealt with salesmen at MontgomeryCycleCenter... depending who you get, they arent very helpful (i had one guy try to talk me out of buying a GZ lol). Blackmans in Emmaus ... GREAT salesmen there. They will encourage you to sit on all their bikes, answer any questions you have, give suggestions and are generally very nice to deal with. Not once did they ask 'so, whats your price range' which irritates me when they ask that (if you lowball, they dont want to waste time with you). I told them i was 'shopping' for a bike and was unsure what i wanted ... they swooped right in and helped me out.