#2 is not valid for me. Lots of options. I really suppose it will depend on the price and availability.
Would love to have another 1979 LowRider (my first Harley)
Would also like to do a nice PanHead on a Softail frame.
Well not my second bike but my 5th bike in the garage will finally be a bagger. But not the kind you would normally see on this forum. Its actually (minus fairings and bags) smaller and lighter than than my sporty. The 108 HP will make it nice Picking it up tomorrow.
If I could afford a second bike I would track down an '05 FXDX with the 88 and 5 spd for solo riding around town. I love my roadie, because it is great two up and on the interstates, but I miss the '05 FXST I had to trade to get there.
I built this over last winter. It started life as a 1977 Sportster XLH1000. The thing is a blast to bebop around town. Not saying this would be my number one choice but for what I have into it I like it.