Don't be afraid to get what you like. But I recommend you ride some other bikes as well. You started in the right place with a small dirt bike, now go ride some standards, some cruisers, a sport tourer or two (Buell Ulysses!!!!) and then ride the two Sportsters. Then get what you like. Never buy a bike you haven't ridden, even if the dealer won't allow a test ride and you just gotta have one. Beg friends, look in the want ads for test ride opportunities, travel to far away friendly dealers if you have to, or look for dealer-sponsored events like the Honda Hoot.
Test rides are always available at those things.
You do have a license don't you? If not, get to a motorcycle safety class and get one. Don't even think of buying a road bike before you go through that training and become licensed.
If you still can't find one to ride, talk to those who own the bikes you want, go to online owners groups or ask MOrons. Oh, you already did.
If you're looking for a sound investment, try mutual funds.