Wow, a lot of great feedback here. Many thanks guys.

To answer Rains2much question, it already has a Super E and EV27 installed. I will also count the rear sprocket teeth when I get home. Novice question here, but does 10:1 pistons automatically mean needing new heads to go with them?

Gotta be honest, I was hoping for some cheaper solutions, but "buy a bike with a bigger engine" cracked me up. Like bustert said, I know older HD's got up to pretty good speed, even with lower compression, so IDK what made that happen...

While I love working on my bike I'm confident saying I'm no real mechanic (just learning bit by bit over the past couple years), so head jobs are going to be a fair amount of research for me but I won't rule it out.

 

Check our the VOES, it might have a broken wire or be bad internally

 

voes is an EPA thingy, nothing more, nothing less
before voes, there was mechanical advance and before mechanical advance was fixed timing.
i do not run a voes and i run the lowest curve on the ultima, primarily do to the fuel they hawk nowdays.
shoot, i had a fixed ignition suzuki b100p that would do 80 mpg and that was 120cc.
as far as heads, you probably can get by using them as is. the compression boost just improves efficiency and really does not change air flow unless you are using domed pistons which would take up some of the swept volume.
your leanest way is ratio change. back in the day, average engine rpm was 3200+ and hauled around 4000# bodies, now, less than 2000# bodies under 2000 rpm.
i had a 5th wheel 11,200# gross and 930# pin weight and my silverado with 5.2 and a 3:73 rear end would pull it anywhere i wanted to go and knock down 12 mpg avg.
jump ahead, new trailer 1/2 in everything, and the truck could not pull it, had to go to 4:11 rear gear set to stop tranny hunting, would rather lose some mpg than a tranny. i brought the 7 mpg up to 11 mpg.
the diff, it was a travel trailer and was like dragging a parachute. the 5th wheel, the truck tucked under it so air drag was less.

 

If you`re saying that cars weigh under 2000lbs , I`d love to see some.

 

What exactly does this mean?

An EVO era Softail is not a machine for high speeds, no matter how much power it has...

You will not need to do any correction for speedometer if you change any sprockets, your bike`s speedometer is driven by the front wheel.

 

Disagree, it is not just an EPA thing.

The VOES was a way to add some more control to the spark timing, because the early electronic ignition systems did not have a way of knowing what the throttle setting was.

The VOES retards the timing when you crack open the throttle, this helps prevent detonation.

The timing goes back to the more efficient advanced timing when cruising.

 

I don’t know if I would go that far to say that, my Evo Springer was no slouch, mine is bike #16 and #13 was my Buddy on his V rod, I caught him snoozing with RT

 

I’ve done everything I know to help with the higher mph.. alignment of motor, tranny frame, neck adjustment, fall away, tire balancing, wheel alignment, shocks, tires… I’ve had it at 125 and it’s still a scary thing.. my hardtail at 140 was about as stable as my springer at 125.. I sure would like to get more stability out of it. Another 10 mph would be awesome.

 

Other than time slips I have no idea how fast my Springer was capable of. That was one of my best slips, decent 60 on regular tire, and beat the Vrod for the first time.
I would now with phone GPS. The times I had the room to wind her out, it went past the factory 120 mark was pointed back at my six, and the needle just looked possessed after that, it was bouncing and erratic and well you can’t look at the dash that long. Surprised a lot of street light commandos when a old Springer hole shot the **** out of them.