The way it looks all across the world, I see its only downhill for Harley from here and I dont think its only HD and its products or marketing to blame, but HD is almost approaching the same stage as the Kodak-digital-revolution-doom-stage for a variety of reasons.
The whole Cruiser motorcycle market has always been an emotional segment, where performance, riding position, weight etc are not optimized or on a razor edge. When people didn't want something too fast, but still needed a road presence & large engine displacement, not too complicated but have most of the basic essentials and easy to maintain, not too high to flatfoot but still comfortable as a sofa etc etc they went and bought a cruiser. Anyways, in that cruiser group those that specifically wanted something with the whole Heritage bang-bang or The Original blah blah etc and didnt mind a little less reliable but costlier to buy and maintain bike they went and bought HDs (I even had a BMW T-Shirt that said "If Harley made an aircraft, would you fly in it??"
). On the other hand, those that thought a little less heavenly, and probably with less to spend, went and bought the metric cruisers from the Japanese big 4 or the limited offerings from Europe. The cruiser segment had a golden run for many decades or rather a century, mostly in North America and to a lesser proportion around the world and now it looks like that segment is neither getting a big number of returning buyers or new buyers and its shrinking at a much faster pace than glaciers around the world. Anyways, how many new model launches of the Intruder or Star or Shadow or Vulcans have you seen in the last couple of years from Japan? Besides, almost a decade back most of the high-profile S&S engined custom bike makers closed shop after a very brief & flamboyant few years of run. Anyways in India these latter 2 categories dont have much takers, due to image and price considerations respectively.
Bikers' priorities and needs have drastically changed and thats where Adventure bikes, Retro bikes, the mid displacement segment etc have created separate markets for themselves and it looks they are here to stay for sometime before probably some other newer trend catches up, but certainly doesn't look to be slanting anywhere even remotely towards the big-fat-pig cruiser market.
In parallel, the premium Europeans went into overdrive with razor sharp designs and super-duper technology (frankly some are blatantly over engineered and prone to irritating niggles etc) and hence many of the well healed buyers have replaced their yearly or biennial 'upgrades' from HD garage queens to other queens from BMW, Ducati, etc or added a 2nd or 3rd Retro Classic bike to their stable. The Japanese have also matched the European offerings with lesser expensive but more reliable bikes be it the Africa Twin, V-Strom 1050, CB1100, Katana, Z900RS etc and ofcourse the great Indian story of apna own RE with its successful Himalayan and the 650 twins which has sets its sales charts on fire all across the world. Imagine if RE instead made a Harley type sofa cum bed cruiser, we know where that would have headed!
In INDIA also, people seem to be losing interest in the Sportster models which sold well as that has not seen much design or tech updates and seems to be produced in cruise control mode. The Bonnevilles, the RE Twins, Scramblers etc have eaten into that segment, while many others have now lost their infatuation for Harley and moved to Adv bikes like Versys and V-Strom (some of which mainly due to backaches, vibrations and bumpy rides!). While the bigger bikes from Harley have got more expensive and with our own bad roads, speed-breakers, possibly even narrow bike lanes at toll gates, and having endured the unending agony of scrapping under body parts on our notorious roads due to the low ground clearance for many years plus long wait for critical spares etc as many have reported, a good number of potential Large displacement Harley buyers seem to be heading to buy a R1250GS Adventure or Ducati MS1250S etc with all bells and whistles, although many of those bikes will rarely see the gravel trails other than stand up riding when there are potholes on our main roads!
And for Harley, with too much of tradition in their DNA, any change from its conventional offerings has been less than successful in its cash register- so once bitten, twice shy, examples include its single cylinder bikes, opposed engine experiment after World War, or more recently the V-Rod, 1200XR and the present Street 500/750 range. Going further, I don't see much fireworks either with the Electric Livewire or the Pan America, both of which I am presuming are going to be priced thru the roof in India for exclusivity.
With such wide presence worldwide, they may perhaps limp for some more years and although may not shut shop, they may remain an also ran participant, and probably have a limited operation in India.