I see Indian mentioned a few times; I have an Indian CDH and a GSA; for me, I prefer to use the Indian for long distance solo touring particularly if i know the roads will be good, Ive had it 7 years and have had no issues with it at all, although it is very basic (no Ride Command etc) but has cruise control. It is all day comfortable. I also had the full dress tourer Roadmaster and again had no issues with it and it was a great solo or two up tourer, loss of my job though meant it had to go.
Ref the stupid mudguard thing, they are very practical and keep crap of the bike and rider so they are very functional; however they have stopped using the (valanced Fenders) as they call them on virtually all models now and went to a more conventional style which I think is a shame as it was a unique feature of the range.
The GSA is now reserved for two up touring as my wife prefers it to the Chief, that said I upgraded the Chief suspension last year with the adjustable air shock from a Roadmaster and she is yet to have a long run on it since but its a vast improvement. I ran the Indian alongside a street Bob for 18 months and for me the Indian was the better bike so the HD went.
I find the GSA uncomfortable, after about an hour i'm squirming in the saddle, my knees ache and my shoulders ache. Up and back risers helped the shoulders but no amount of changes (seats etc) on any GS I've owned has cured the arse ache or knee problems. I have none of these issues on the Indian, I can stretch out on it and its all day comfortable despite it having a stock seat.
If it were not for my wife I would not own a GSA, it is her favourite bike and for her the most comfortable and that's the only reason for having it, it is therefore the least used bike I have as two up riding is rare, I mostly ride solo. The GSA is a great performing and handling bike and the obvious choice if the roads are rough or I need to carry a load of luggage, but I just can't get comfortable on it over long distance.
It it were my choice I'd get rid of the GSA and the Chief and replace them with an Indian Pursuit (tourer based on the Challenger platform).
I take Atts point though ref the Puch Maxi; touring on a small bike resets the mind and dare I say is more fun and adventurous, there is no hurry to get anywhere so no need to rush (you can't anyway) you actually take in more of the environment you are traveling through. Of the bikes I have at the moment the most utilised are the small ones, Honda Monkey has done big trips with camping gear etc and is more comfortable than the GSA (and i'm 6' 2") you've just got to give yourself more time.