I am 6' last time I got weighed I was up to about 270
I ride a Sportster. I got it used, so I'm not entirely sure it is still an 883, but it has a Screamin Eagle air cleaner and straight through slip ons (no baffles). I put taller bars on it and converted it to mid controls (I know, most people will tell you that you NEED forwards, forwardsare not for performance. I rode dirt bikes before and really like the mids) My bike will haul ass up any hill and I live in mountain country, the Pacific Northwest. I ride 40 miles one way to town, it can get uncomfortable, but I have back problems anyways. You can also drop in Road King air shocks pretty cheap, I got a set for like $50, but I went back to stock because I like the low look, I have tail dragger fenders.
The only reason I can see to get a "bigger" bike is if I get a lady friend rideing on the back and even then I will never sell this sporty. I see road kings for $8,000 occassionally, that is probably what I would buy, but I also like the Dynas and FXR. I like the few Dynas that come with mids, most notably the Super Glide Custom, not sure if they are offering that this year?
I got my bike used three years~ ago for $4000, it's an '04, so it was about 7 years old with 10,000 miles and looked brand new. You can't find deals like that on big twins. For me, financially, there was no other option. If I was buying new today, if I had the money, or stupidly didn't mind payments, I'd buy a Dyna for about $2500 more. IMO new sportsters are not worth the $10K.