Kittty - this has been a fun exercise, thinking about classic bikes.
I think the HD is the fit for what you describe. The dealer near me lets me demo the bike I want to buy for up to half a day with no obligation. I have bought 2 bikes from them before, so they know I'm not BSing them. I suspect your dealer would do the same. That gives you a few hours in the saddle to see if it feels, sounds, looks like the right fit.
Then it might just be about timing. Fall is a great time to buy a bike. Model year is coming up and people and dealers don't want to have to store a bike over winter.
That is my unrequested buying advice :-)
I'm sure whatever you decide will be fun. Enjoy the ride.