This is actually a pretty good thread as I have 96" Road King and went thru a lengthy decision process on power upgrades, with the goal of not ruining reliability.

Last year I bought new wheels, tires, rear shocks and contemplated the Fuel Moto 107 Package. I ended up buying just a cam kit, leaving myself the option to do the jugs and pistons later. I've got maybe 1500 miles on the cam upgrade, and am struggling to tear apart such a great running engine in search of more power. I went a little big on the cams, but I ride solo and not long distance, so midrange+ is perfect for me and the Wood 555s should work great with a stock headed 10.25:1 CR 107.

My point is that one doesn't necessarily need to tear apart the 96" to enjoy the bike....exhaust, intake, tuner, cams, and call it a day. I love riding my stripper King up and down the California Coast. I'll add more power eventually, but I'm not finding myself in hurry to tinker with it any time soon. But then again, I bet that 107 is fun to ride...

Question for the engine guys....is 96 to 103 a good bang for the buck, keeping compression stock or a little higher with the thinner head gaskets? Or budget allowing, just for the 107 with compression?

 

You can ask 10 different people that question and get 13 different answers. The reason I decided to stay with the 103 upgrade (aside from the obvious budget constraints) is that it's still essentially a stock motor. These are all factory parts and should something do wrong, it'll be that much easier to find replacement parts.
The general consensus is that the 103 upgrade is a very good bang for the buck.

 

The 103 with the thinner head gasket and the right cam would be a great bang for the buck upgrade from the 96 which is anemic in stock form. The runout can be a big deal if it's way out but more often it's a non issue when you get in there.

 

What I found by doing my engine swap was. Compared my 96” with 26H cams to my 103HO stock, the 103HO pulls about the same at low end but keeps pulling throughout the rev band. It’s just a smoother power all around. Plus I am comparing a 103HO with 10000 miles to a cammed 96 with 92000 miles. This with a new compensator, clutch, swing arm bearing/bushings made this old bike feel almost new. I’m not even jonesing over newer bikes anymore..lol. Well maybe a little...

 

The whole “bang for the buck” thing! Depends... if ya can pick up good cylinders and pistons cheap like the OP and I did it is good BftB. If ya are boring cylinders and buying new pistons, not so much. 107 would be about the same cost giving at least 5 to & hp more. Either way the the 96 low compression makes a bore necessary for any performance upgrade.