Only true way to know whats best is to test ride several and then look for what feels best in your price range. I love my Heritage and at 5'10" it fits me perfect. Softails are more of a sit in bike where the tourings are more of a sit on feel.

I 2-up ride 90% of the time and recently went 760+ miles in 3 days cruising around and had a bag strapped on the luggage rack and we didn't have 1 issue. Touring bikes are typically better for 2-up but I personally like the feel of sitting in the Heritage. With that in mind tho I do plan to also get an Ultra one day for taking long trips cross country.

 

Can't go wrong with a Deuce or a Night Train if it feels good for you. Suspect you'll enjoy those bikes too if you're used to the low, long Vegas. They certainly hold their value too. I have a Deuce and my buddy has a Train and we love 'em. Leaving in a few week with him for 3 days in the mountains. I will say that I'm considering a Heritage or something like that if I end up having a 60 mile one-way commute every day in the near future.

 

You have a wide selection of the ones you like. In fact, a little too wide. I think the advise given about test riding is the way to go. You really need to narrow it down to what frame fits you and go from there. As big as you are I would think a touring frame would fit you well. Have you looked at the Road Glides?
Also, you really need to figure out what kind of riding you will be doing. 2 up with some longer trips. 1 up long trips or just short trips in urban areas. That's why I have 2 bikes. The Heritage is one that does both fairly well and a Road King will as well. But on the open road 2 up, it doesn't compare to the Ultra. So I down keep it stripped down for the short solo rides. For a guy you size and if you are wanting a bike that can do both, I think a King would probably be your best bet, but you need to ride them all.

 

I suggest getting the newest bike you can since you only have so much you are willing the spend. I think you can get a relative new Dyna for under 15 g's.

 

Yeah I'm gonna do demo days in October. Road Glides are nice, I dig the dual headlamps, but they're too expensive for me right now. I plan to spend less than 10k.