Don't touch the Harley!
As a rider of many (!) years I have only recently taken the Harley route and can only say that it was a BIG mistake.
Like you, I use a scooter for every day work, a 200cc Vespa. Inevitably things occasionaly go wrong with it. When they do, my local dealer usually has the parts in stock or can get them within a few days. He always provides me with a courtesy bike to keep me mobile. I have had similar experience with the main Japanese / Triumph dealer here in Bristol.
I took the plunge and after some deliberation - much like you invested nearly £10,000 on a brand spanking new Harley Super Glide which arrived on 1st March. After just ove 2 weeks it wouldn't start and this was diagnosed as a problem with the flywheel ring gear - a shame but these things happen.
Since then it has resided at the Bristol Harley dealer, Riders of Bristol. Firstly they have been unable to get the parts from Harley (this is really significant since all the 'big' Harleys have the same engines and thus the same parts). They are now saying that it will be at least the end of the month before these arrive (and, of course I believe that !)
Riders of Bristol are 'unable' to provide me with a loan bike (this is how much customer care you get from them), as a result, having spent a near 5 figure sum on a new bike I am without one for at least seven weeks and my guess is a lot more.
In summary therefore, get a cruiser they are great. Don't get a Harley because the supply of spares is terrible. If you DO decide to get a Harley make sure that you get guarantees from your dealer that in the event of a breakdown they will be able to keep you on the road with SOMETHING, even if its just an old banger of a 250,(unlike Riders of Bristol ).
So its a big HI. to everyone and I hope you are enjoying the great riding weather we have had recently - I only wish that I could be out there with you!