Well I say try a Road King. Great two up tourer that still seems light enough to make small runs on. Also, look at a Triumph Rocket III. Those things are big. Also, don't be afraid to look at a Victory. Then there's the Yamaha Raider, and Road Liner. I know they aren't Harleys but if you aren't comfortable...

 

for what you are wanting a road king sounds right to me. Tons of my friends have them and love them. I seem to be the only one holding out on the dark side. But I ride solo so its not such an issue for me. Rent a couple of your fav. bikes from HD and ride them or hold out for the test ride days. they should be coming up very soon , august is usually new bike model time. Once you find a bike you love you can figure out the other stuff.

 

I'm gonna get shot for this...
The Honda looks like it fits you better than the WG, BUT it's a Honda. The Dyna didn't look bad with you on it. Test ride your favorite Harleys, and even the Honda and go for what has the best looks and comfort in your opinion

 

Just checked out your pic of you on your friends softail. You look perfectly fine on it. Don't buy a bike to make someone else happy, buy one in your budget and doesn't kill your **** or legs riding it

 

Wait for it........which is the first one to come to mind right now? That is the one you want to get! Now what are you waiting for????

 

It's all about how you change the bars and the controls. When I went on that motorcycle ergonomic sight, the Honda actually has a tighter knee angle than the Wide Glide. The Honda is just raked out more to appear larger. From the steering head back it's not any bigger though. I noticed your friends softail has apes on it also. This is how you can make your bike fit you better. I'm 6'3" and 265lbs. I ride a super glide sport with forward controls and street slammers. Other than the seat it is very comfy. I may add an extension to the controls, but that it.

 

Ok you have basically got every opinion you can so I am not sure mine is going to matter much however IMO I would not get a dyna if you plan on doing alot of 2 up riding. With you saying both you and or wife are good size people your going to be much more comfortable on a bagger. If I was in your position I would buy a street glide fantasic looking bike when riding alone and 2 up also large enough for what your looking for. However you must not settle for what is suggested you must buy what you like best or you'll never be truely happy with the purchase and thats no fun!!! Good Luck

 

If you're a new rider, you might want to consider buying a cheap used metric (Japanese) bike to learn on. There are plenty to choose from on Craigslist. Ride that for six months, or however long it takes for you to get confident in your riding skills. Once you're comfortable and have a little riding experience under your belt, go get a HD bagger. If you're going to be riding with your wife most of the time and you are both large people you'll both be happier on the bagger. My advise would be to get an Ultra Classic, or Road Glide Ultra. Your wife will love you for it. I love the Wide Glide, but the new ones with the factory lowered suspension just wouldn't be a good fit for two large people to ride I don't think.

 

Get the WG. Just my .02

 

6'3" here, on a wide glide. Have corbin seat, 16" apes, and 3" extended forwards. PERFECT!

Like everyone else has been saying, there is a LOT you can do to make your fit more comfortable. And you're not too big for any of those.