For what its worth I found from going to a custom to my heritage. Its the windshield that helps the most on long days in the saddle. You are a big parachute on the highway and I was amazed at how much a windshield helped !! Next look at your seat I don't think the fat boy has a very comfortable seat. Look at mustang seats. And I would also adjust you shocks for your riding weight., before looking to replace them. Highway pegs and new handle bars you can do much later if you want but the wind shield and seat... 300 miles a day would be no problem..swifty

 

I think it is a matter of personal preference. I wanted better wind protection, so I went with a Batwing fairing. Added a radio and speakers for some tunes. Added some hardbags and a seat that I found to be comfortable. Fits my riding style....looks like a "Softglide"

 

Fairing, fangs, different seat, Heritage bars, 422's, Ricors front suspension and leave bike at stock height.

 

Mustang wide solo with an Airhawk R on top, Avon air ride grips, 3 1/2" / 1" pullback risers, LRS recurve windshield, Linbar, saddlebags and Nelson Rigg waterproof bag. music streaming from the Android over a Sena SMH1. 15 weight Bel Ray in the forks
300 miles is a piece of cake and I want to keep going .....

 

I love my Heritage, and would tour on it all the time, except for two things I can not fix. My wife hates the seating position. The high rear seat puts her head right in the wind and unless I add another foot to the windshield, no fix for that. The other is cruise control. We put in a lot of 500+ mile days and that little set screw just does not cut it. When touring, a functioning cruise control is a real blessing.

 

I'm with the rest. Set the bike up to fit you first. Nothing else will matter if you are not right on the bike.

Then bags, windshield or bat will make it easier to deal with.

Or you can create your own soft-bagger.

 

My Wife had the same issue.

My stock windshield was a standard 17".
Which was fine for me, but the Wife complained of buffering.

I got a 20" Klock Werks Billboard Flare windshield.
It not only was 3" taller, but due to it's design it deflects the air about 3" above the shield, resulting in moving the air about 5-6" higher than the stock windshield.

This all but eliminated the buffering she was experiencing (so she says).

 

There is zero vibration in my Softail at any speed I've ridden at, up to around 90 or so. I've tested several touring bikes and couldn't wait to get back to mine

 

My Streetglide would put my hands to sleep after 15 minutes, I'm so glad to be back on a Softail. No vibration, much more comfortable, and once I get tunes on it I'll be all set!

 

For my bike's touring comfort I add my windshield, reshaped and padded stock seat and saddlebags. I am still using the stock shocks and lowered 1.5" front and rear. I have done several 400+ day rides and don't feel too bad at the end of the day. I do plan on a rear suspension upgrade this winter. Still undecided on going with 422's or Shotgun Air.