The ev27 seems to get a lot of love in this forum. I'm more of a Bob Wood fan myself. W6 with some collapsible pushrods and call it done.

The CV will do well with the enrichener screw turned out some as well as fattening out the jets. It is a good carb for sure.

 

That old and that few miles on it, you better check the grease in the wheel bearings. I'll bet it's dried out and not lubricating like it used to. Believe me, you don't want to go through what I did when the bearing spacers welded to the axle on mine (got a '98 with only 28,000 miles on it and found out the hard way the grease had dried out).

 

Welcome, the 46 is still a good light bike cam, the valve springs won't be necessary,
a Cometic .010 base gasket usually gets the deck height close to zero,.060 off the heads and a .030 head gasket should put cranking compression about 185psi with the 46.
Good three angle valve job and very little port clean up, intake manifold will probably need a small trim for clearance between the heads.
I did the same build to a '97 softail, it had a S&S E carb and V&H big radius pipes, simple Dyna S ignition, no lifter noise, the thing flew, best sounding Evo I heard to this day, regret letting it go.

 

 

If your gonna pop the heads have them worked to bring the comp up to 9.5:1 and through in an EVL 3010. A friend of mini, Ruggs59, on his 98 Road King put on SE heads and the EVL cam and I must say I was very impressed with the way it ran. Power range was every where...

 

Shameless plug but i have a dyna2000 ign
in the classified section

 

Your pic of the Road King air filter cover is a work of art!

 

 

 

Here is his add in the classified section
https://www.hdforums.com/forum/evo-e...dyna2000p.html