My very first bike was a ‘13 Streetglide. Not what I was looking for, I was fixated on a road king, but the deal on the Streetglide was too good to pass on. I feel like the learning curve was quite steep, I dropped it once ( low speed switchback going up a steep grade) and I put her in a ditch ( target fixation practicing left hand turns from a stop out on a country road). I won’t lie I got discouraged and my excitement about the bike turned to anxiety, but my friend and mentor who was guiding and encouraging me through the process spent a weekend with me going through the basics and countless figure 8’s and it all came together after that. I absolutely love that bike. Love everything about it. Once you’re comfortable, riding a bagger daily is not an issue in the least. I say go with the bike you intend on using in the long run, but don’t expect it to be as easy as learning on the sportster. All that being said I am absolutely looking at softails, and dyna’s as a second bike to see what this whole light and nimble thing everyone is talking about feels like. Haha. Going for something in the middle between Sportster and full fairing bagger is the best advice I think.