A 2000+ Heritage Springer would be a great second bike. Purchased a new 99 and 2000 Heritage Springer, sold both of them. Miss them terribly. Especially the 2000. If Harley ever re-introduces the Heritage Springer with all the updates found on the 16 Heritage Classic I would have a hard time controlling myself.
Side note: met one of the HD employees that built the chrome Springer front end. She said it will never return, said it was extremely expensive and time consuming to build. She also said it was too expensive to maintain. Those that own a Heritage Springer have a real classic.
My first real motorcycle was a sportster in 1964, so my other bike is a sporty Bronson tribute. Use it for errands, sometimes commute, and short canyon rides to clear the head. My 3rd ride is an '81 Yamaha XS650 Storm.
I had a similar sidecar as yours a few years back...Velorex 562 E. Lots of fun. That's why I'm doing it again!
563 with the heavier frame. It works for what I needed it for. granddaughter in wheel chair. Did not want her left out. Wife had suggest buying a third bike for that . But I came up with sticking one on my old FB.
"second bike"? uuummmm... Well, I have two evo sporties and one of those is the "main ride", although the weather just now... And I have an '87 evo FX that's ride-able but slated for some surgery to the electricals. And there's the two Yamaha Specials...one's in a rigid. But the bike I really miss is the old WL in a light custom swingarm frame; long gone to the tweeker community, alas! Really miss that flathead. Bike I'd like though would be a mid 60's BMW R65...that's one I never had. Quite frankly none of the new bikes have much appeal to me - and I'd include the evo sporty and FX in that - but at least they don't have computers!